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Title: Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations

Abstract

A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.

Authors:
ORCiD logo [1];  [2];  [1];  [3];  [1];  [1];  [1]; ORCiD logo [2];  [3]
  1. Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, China
  2. Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
  3. Department of Chemistry, Lehigh University, Bethlehem, USA
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1509518
Grant/Contract Number:  
[SC0009363]
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
[Journal Name: Chemical Science Journal Volume: 10 Journal Issue: 20]; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Yang, Yi, Zhou, Qinghai, Cai, Junjie, Xue, Teng, Liu, Yingle, Jiang, Yan, Su, Yumei, Chung, Lungwa, and Vicic, David A. Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations. United Kingdom: N. p., 2019. Web. doi:10.1039/C9SC00554D.
Yang, Yi, Zhou, Qinghai, Cai, Junjie, Xue, Teng, Liu, Yingle, Jiang, Yan, Su, Yumei, Chung, Lungwa, & Vicic, David A. Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations. United Kingdom. doi:10.1039/C9SC00554D.
Yang, Yi, Zhou, Qinghai, Cai, Junjie, Xue, Teng, Liu, Yingle, Jiang, Yan, Su, Yumei, Chung, Lungwa, and Vicic, David A. Wed . "Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations". United Kingdom. doi:10.1039/C9SC00554D.
@article{osti_1509518,
title = {Exploiting the trifluoroethyl group as a precatalyst ligand in nickel-catalyzed Suzuki-type alkylations},
author = {Yang, Yi and Zhou, Qinghai and Cai, Junjie and Xue, Teng and Liu, Yingle and Jiang, Yan and Su, Yumei and Chung, Lungwa and Vicic, David A.},
abstractNote = {A bis-trifluoroethyl coordinated nickel/bipyridine complex has been developed as efficient precatalyst for diverse Suzuki-type alkylations which features unconventional precatalyst initiation mode.},
doi = {10.1039/C9SC00554D},
journal = {Chemical Science},
number = [20],
volume = [10],
place = {United Kingdom},
year = {2019},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C9SC00554D

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Cited by: 3 works
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Works referenced in this record:

A perfluorometallacycloheptane complex of nickel bipyridine
journal, November 2017


Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
journal, June 2011

  • Lu, Zhe; Wilsily, Ashraf; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 133, Issue 21
  • DOI: 10.1021/ja203560q

Alkyl-Alkyl Suzuki Cross-Coupling of Unactivated Secondary Alkyl Chlorides
journal, August 2010

  • Lu, Zhe; Fu, Gregory C.
  • Angewandte Chemie International Edition, Vol. 49, Issue 37
  • DOI: 10.1002/anie.201003272

A Modular, Air-Stable Nickel Precatalyst
journal, April 2015


Alkylations of Arylboronic Acids including Difluoroethylation/Trifluoroethylation via Nickel-Catalyzed Suzuki Cross-Coupling Reaction
journal, August 2015

  • Zhang, Xiaofei; Yang, Chunhao
  • Advanced Synthesis & Catalysis, Vol. 357, Issue 12
  • DOI: 10.1002/adsc.201500346

Reductive elimination of Et—Et from NiEt2(bpy) promoted by electron-accepting aromatic compounds
journal, May 1997


Oxidative C–C Bond Formation Reactivity of Organometallic Ni(II), Ni(III), and Ni(IV) Complexes
journal, December 2016

  • Watson, Michael B.; Rath, Nigam P.; Mirica, Liviu M.
  • Journal of the American Chemical Society, Vol. 139, Issue 1
  • DOI: 10.1021/jacs.6b10303

Preparation and Properties of Monoalkylnickel(II) Complexes Having a Phenoxo, Benzenethiolato, Oximato, β-Diketonato, or Halo Ligand
journal, July 1981

  • Yamamoto, Takakazu; Kohara, Teiji; Yamamoto, Akio
  • Bulletin of the Chemical Society of Japan, Vol. 54, Issue 7
  • DOI: 10.1246/bcsj.54.2010

Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct CC Bonds (Nobel Lecture)
journal, May 2011


Accessing perfluoroalkyl nickel( ii ), ( iii ), and ( iv ) complexes bearing a readily attached [C 4 F 8 ] ligand
journal, January 2015

  • Yu, S.; Dudkina, Y.; Wang, H.
  • Dalton Transactions, Vol. 44, Issue 45
  • DOI: 10.1039/C5DT01771H

Density Functional Theory Studies of Negishi Alkyl–Alkyl Cross-Coupling Reactions Catalyzed by a Methylterpyridyl-Ni(I) Complex
journal, May 2008

  • Lin, Xufeng; Phillips, David Lee
  • The Journal of Organic Chemistry, Vol. 73, Issue 10
  • DOI: 10.1021/jo702497p

Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide
journal, May 2017

  • Juliá-Hernández, Francisco; Moragas, Toni; Cornella, Josep
  • Nature, Vol. 545, Issue 7652
  • DOI: 10.1038/nature22316

Mechanism of CC coupling reactions of aromatic halides, promoted by Ni(COD)2 in the presence of 2,2′-bipyridine and PPh3, to give biaryls
journal, April 1992

  • Yamamoto, Takakazu; Wakabayashi, Shoichiro; Osakada, Kohtaro
  • Journal of Organometallic Chemistry, Vol. 428, Issue 1-2
  • DOI: 10.1016/0022-328X(92)83232-7

Complexes of Ni( i ): a “rare” oxidation state of growing importance
journal, January 2017

  • Lin, Chun-Yi; Power, Philip P.
  • Chemical Society Reviews, Vol. 46, Issue 17
  • DOI: 10.1039/C7CS00216E

Synthesis of gem -Difluoroalkenes via Nickel-Catalyzed Reductive C–F and C–O Bond Cleavage
journal, November 2018


The unique fluorine effects in organic reactions: recent facts and insights into fluoroalkylations
journal, January 2016

  • Ni, Chuanfa; Hu, Jinbo
  • Chemical Society Reviews, Vol. 45, Issue 20
  • DOI: 10.1039/C6CS00351F

Radical Switch Reaction. A Novel Reaction between Two Free Radicals in a Solvent Cage
journal, January 1987

  • Kobayashi, Michio; Gotoh, Michiko; Yoshida, Masato
  • Bulletin of the Chemical Society of Japan, Vol. 60, Issue 1
  • DOI: 10.1246/bcsj.60.295

Nickel(I) Aryl Species: Synthesis, Properties, and Catalytic Activity
journal, January 2018

  • Mohadjer Beromi, Megan; Banerjee, Gourab; Brudvig, Gary W.
  • ACS Catalysis, Vol. 8, Issue 3
  • DOI: 10.1021/acscatal.8b00546

Linear Bis(perfluoroalkyl) Complexes of Nickel Bipyridine
journal, November 2011

  • Yamaguchi, Yoshitaka; Ichioka, Hiromi; Klein, Axel
  • Organometallics, Vol. 31, Issue 4
  • DOI: 10.1021/om2012776

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling between Heteroaryl Iodides and α-Chloronitriles
journal, August 2015

  • Kadunce, Nathaniel T.; Reisman, Sarah E.
  • Journal of the American Chemical Society, Vol. 137, Issue 33
  • DOI: 10.1021/jacs.5b06466

Stable, Well-Defined Nickel(0) Catalysts for Catalytic C–C and C–N Bond Formation
journal, May 2018


Transition metal catalysis in confined spaces
journal, January 2015

  • Leenders, Stefan H. A. M.; Gramage-Doria, Rafael; de Bruin, Bas
  • Chemical Society Reviews, Vol. 44, Issue 2
  • DOI: 10.1039/C4CS00192C

Transition metal–catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry
journal, April 2017


Nickel-Catalyzed Cross-Coupling of Functionalized Difluoromethyl Bromides and Chlorides with Aryl Boronic Acids: A General Method for Difluoroalkylated Arenes
journal, July 2014

  • Xiao, Yu-Lan; Guo, Wen-Hao; He, Guo-Zhen
  • Angewandte Chemie International Edition, Vol. 53, Issue 37
  • DOI: 10.1002/anie.201405653

Advances in metal-assisted non-electrophilic fluoroalkylation reactions of organic compounds
journal, February 2015

  • Lantaño, Beatriz; Torviso, M. Rosario; Bonesi, S. M.
  • Coordination Chemistry Reviews, Vol. 285
  • DOI: 10.1016/j.ccr.2014.11.004

Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Amides via Site-Selective N–C Bond Cleavage by Cooperative Catalysis
journal, October 2016


Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective
journal, January 2011


Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides
journal, October 2013

  • Biswas, Soumik; Weix, Daniel J.
  • Journal of the American Chemical Society, Vol. 135, Issue 43
  • DOI: 10.1021/ja407589e

Enantioselective, Nickel-Catalyzed Suzuki Cross-Coupling of Quinolinium Ions
journal, November 2013

  • Shields, Jason D.; Ahneman, Derek T.; Graham, Thomas J. A.
  • Organic Letters, Vol. 16, Issue 1
  • DOI: 10.1021/ol4031364

Palladium-Catalyzed Suzuki–Miyaura Coupling of Aryl Esters
journal, January 2017

  • Ben Halima, Taoufik; Zhang, Wanying; Yalaoui, Imane
  • Journal of the American Chemical Society, Vol. 139, Issue 3
  • DOI: 10.1021/jacs.6b12329

Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling Catalyst
journal, October 2006

  • Jones, Gavin D.; Martin, Jason L.; McFarland, Chris
  • Journal of the American Chemical Society, Vol. 128, Issue 40
  • DOI: 10.1021/ja063334i

Decarboxylative Cross-Electrophile Coupling of N -Hydroxyphthalimide Esters with Aryl Iodides
journal, April 2016

  • Huihui, Kierra M. M.; Caputo, Jill A.; Melchor, Zulema
  • Journal of the American Chemical Society, Vol. 138, Issue 15
  • DOI: 10.1021/jacs.6b01533

Organometallic Aspects of Fluoroalkylation Reactions with Copper and Nickel
journal, August 2013


Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes
journal, April 2017

  • Poremba, Kelsey E.; Kadunce, Nathaniel T.; Suzuki, Naoyuki
  • Journal of the American Chemical Society, Vol. 139, Issue 16
  • DOI: 10.1021/jacs.7b01705

Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions
journal, January 2009

  • Rudolph, Alena; Lautens, Mark
  • Angewandte Chemie International Edition, Vol. 48, Issue 15
  • DOI: 10.1002/anie.200803611

Nitrogen–Nitrogen Bond Formation via a Substrate-Bound Anion at a Mononuclear Nickel Platform
journal, February 2018


Base-free nickel-catalysed decarbonylative Suzuki–Miyaura coupling of acid fluorides
journal, October 2018


Design, synthesis, and carbon-heteroatom coupling reactions of organometallic nickel(IV) complexes
journal, February 2015


Nickel-catalyzed fluoroethylation of arylboronic acids via Suzuki-type coupling
journal, January 2019

  • Yang, Yi; Cai, Junjie; Luo, Gen
  • Organic Chemistry Frontiers, Vol. 6, Issue 9
  • DOI: 10.1039/c9qo00066f

Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes
journal, April 2016

  • Xiao, Yu-Lan; Min, Qiao-Qiao; Xu, Chang
  • Angewandte Chemie International Edition, Vol. 55, Issue 19
  • DOI: 10.1002/anie.201601351

Recent advances in homogeneous nickel catalysis
journal, May 2014

  • Tasker, Sarah Z.; Standley, Eric A.; Jamison, Timothy F.
  • Nature, Vol. 509, Issue 7500
  • DOI: 10.1038/nature13274

Well-defined nickel and palladium precatalysts for cross-coupling
journal, March 2017

  • Hazari, Nilay; Melvin, Patrick R.; Beromi, Megan Mohadjer
  • Nature Reviews Chemistry, Vol. 1, Issue 3
  • DOI: 10.1038/s41570-017-0025

Copper-Promoted Reductive Coupling of Aryl Iodides with 1,1,1-Trifluoro-2-iodoethane
journal, April 2014

  • Xu, Song; Chen, Huan-Huan; Dai, Jian-Jun
  • Organic Letters, Vol. 16, Issue 9
  • DOI: 10.1021/ol500696p

Nickel-catalyzed direct difluoromethylation of aryl boronic acids with BrCF 2 H
journal, January 2018

  • Sheng, Jie; Ni, Hui-Qi; Bian, Kang-Jie
  • Organic Chemistry Frontiers, Vol. 5, Issue 4
  • DOI: 10.1039/C7QO00934H

Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel
journal, March 2018


Direct Difluoromethylation of Aryl Halides via Base Metal Catalysis at Room Temperature
journal, February 2016

  • Xu, Long; Vicic, David A.
  • Journal of the American Chemical Society, Vol. 138, Issue 8
  • DOI: 10.1021/jacs.6b00053

Photo-Triggered Click Chemistry for Biological Applications
journal, December 2015


Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C–O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols
journal, March 2018

  • MacQueen, Preston M.; Tassone, Joseph P.; Diaz, Carlos
  • Journal of the American Chemical Society, Vol. 140, Issue 15
  • DOI: 10.1021/jacs.8b01800

Synthesis and Reactivity of Paramagnetic Nickel Polypyridyl Complexes Relevant to C(sp 2 )-C(sp 3 )Coupling Reactions
journal, March 2019

  • Mohadjer Beromi, Megan; Brudvig, Gary W.; Hazari, Nilay
  • Angewandte Chemie International Edition, Vol. 58, Issue 18
  • DOI: 10.1002/anie.201901866

Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides
journal, October 2018

  • Wang, Xuan; Ma, Guobin; Peng, Yu
  • Journal of the American Chemical Society, Vol. 140, Issue 43
  • DOI: 10.1021/jacs.8b09473

Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling
journal, June 2016

  • Zhang, Patricia; Le, Chi “Chip”; MacMillan, David W. C.
  • Journal of the American Chemical Society, Vol. 138, Issue 26
  • DOI: 10.1021/jacs.6b04818

Challenging nickel-catalysed amine arylations enabled by tailored ancillary ligand design
journal, March 2016

  • Lavoie, Christopher M.; MacQueen, Preston M.; Rotta-Loria, Nicolas L.
  • Nature Communications, Vol. 7, Issue 1
  • DOI: 10.1038/ncomms11073

A General Strategy for the Nickel-Catalyzed C−H Alkylation of Anilines
journal, January 2016

  • Ruan, Zhixiong; Lackner, Sebastian; Ackermann, Lutz
  • Angewandte Chemie International Edition, Vol. 55, Issue 9
  • DOI: 10.1002/anie.201510743

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
journal, September 2010

  • Owston, Nathan A.; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 132, Issue 34
  • DOI: 10.1021/ja105924f

Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations
journal, December 2012

  • Zultanski, Susan L.; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 135, Issue 2
  • DOI: 10.1021/ja311669p

Oxidative Cleavage of CH 3 and CF 3 Radicals from BOXAM Nickel Complexes
journal, July 2012

  • Klein, Axel; Vicic, David A.; Biewer, Christian
  • Organometallics, Vol. 31, Issue 15
  • DOI: 10.1021/om300342r

Development of an Air-Stable, Broadly Applicable Nickel Source for Nickel-Catalyzed Cross-Coupling
journal, March 2015


Nickel-Catalyzed Allylic C(sp 3 )–F Bond Activation of Trifluoromethyl Groups via β-Fluorine Elimination: Synthesis of Difluoro-1,4-dienes
journal, September 2015


Replacing Conventional Carbon Nucleophiles with Electrophiles: Nickel-Catalyzed Reductive Alkylation of Aryl Bromides and Chlorides
journal, March 2012

  • Everson, Daniel A.; Jones, Brittany A.; Weix, Daniel J.
  • Journal of the American Chemical Society, Vol. 134, Issue 14
  • DOI: 10.1021/ja301769r

Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
journal, September 2015


Oxidation of Ni(II) to Ni(IV) with Aryl Electrophiles Enables Ni-Mediated Aryl–CF 3 Coupling
journal, June 2015

  • Bour, James R.; Camasso, Nicole M.; Sanford, Melanie S.
  • Journal of the American Chemical Society, Vol. 137, Issue 25
  • DOI: 10.1021/jacs.5b04892

Butadiene Polymerization Catalysts. Diethylbis(dipyridyl)iron and Diethyldipyridylnickel
journal, October 1965

  • Yamamoto, Akio; Morifuji, Kazuhiko; Ikeda, Sakuji
  • Journal of the American Chemical Society, Vol. 87, Issue 20
  • DOI: 10.1021/ja00948a051

Enantioselective Construction of α-Chiral Silanes by Nickel-Catalyzed C(sp 3 )−C(sp 3 ) Cross-Coupling
journal, February 2019

  • Yi, Hong; Mao, Wenbin; Oestreich, Martin
  • Angewandte Chemie International Edition, Vol. 58, Issue 11
  • DOI: 10.1002/anie.201814340

Pair production and cage reactions of alkyl radicals in solution
journal, July 1970

  • Sheldon, Roger A.; Kochi, Jay K.
  • Journal of the American Chemical Society, Vol. 92, Issue 14
  • DOI: 10.1021/ja00717a042

The merger of transition metal and photocatalysis
journal, July 2017


Double CF Bond Activation through β-Fluorine Elimination: Nickel-Mediated [3+2] Cycloaddition of 2-Trifluoromethyl-1-alkenes with Alkynes
journal, May 2014

  • Ichitsuka, Tomohiro; Fujita, Takeshi; Arita, Tomohiro
  • Angewandte Chemie International Edition, Vol. 53, Issue 29
  • DOI: 10.1002/anie.201402695

Comparison of dppf-Supported Nickel Precatalysts for the Suzuki-Miyaura Reaction: The Observation and Activity of Nickel(I)
journal, September 2015

  • Guard, Louise M.; Mohadjer Beromi, Megan; Brudvig, Gary W.
  • Angewandte Chemie International Edition, Vol. 54, Issue 45
  • DOI: 10.1002/anie.201505699

The palladium-catalyzed cross-coupling reactions of trifluoroethyl iodide with aryl and heteroaryl boronic acid esters
journal, January 2012

  • Liang, Apeng; Li, Xinjian; Liu, Dongfeng
  • Chemical Communications, Vol. 48, Issue 66
  • DOI: 10.1039/c2cc31651j

Nickel-Catalyzed Monofluoromethylation of Aryl Boronic Acids
journal, March 2015

  • Su, Yi-Ming; Feng, Guang-Shou; Wang, Zhen-Yu
  • Angewandte Chemie International Edition, Vol. 54, Issue 20
  • DOI: 10.1002/anie.201412026

Synthesis of gem -Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling
journal, September 2018


Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides
journal, February 2012

  • Wotal, Alexander C.; Weix, Daniel J.
  • Organic Letters, Vol. 14, Issue 6
  • DOI: 10.1021/ol300217x

Bimetallic Oxidative Addition Involving Radical Intermediates in Nickel-Catalyzed Alkyl–Alkyl Kumada Coupling Reactions
journal, July 2013

  • Breitenfeld, Jan; Ruiz, Jesus; Wodrich, Matthew D.
  • Journal of the American Chemical Society, Vol. 135, Issue 32
  • DOI: 10.1021/ja4051923

Palladium-Catalyzed 2,2,2-Trifluoroethylation of Organoboronic Acids and Esters
journal, December 2011

  • Zhao, Yanchuan; Hu, Jinbo
  • Angewandte Chemie International Edition, Vol. 51, Issue 4
  • DOI: 10.1002/anie.201106742

Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reactions Employing Dialkylbiaryl Phosphine Ligands
journal, November 2008

  • Martin, Ruben; Buchwald, Stephen L.
  • Accounts of Chemical Research, Vol. 41, Issue 11
  • DOI: 10.1021/ar800036s

Carbon–Carbon Bond-Forming Reductive Elimination from Isolated Nickel(III) Complexes
journal, December 2016

  • Bour, James R.; Camasso, Nicole M.; Meucci, Elizabeth A.
  • Journal of the American Chemical Society, Vol. 138, Issue 49
  • DOI: 10.1021/jacs.6b10350

Remote Migratory Cross-Electrophile Coupling and Olefin Hydroarylation Reactions Enabled by in Situ Generation of NiH
journal, September 2017

  • Chen, Fenglin; Chen, Ke; Zhang, Yao
  • Journal of the American Chemical Society, Vol. 139, Issue 39
  • DOI: 10.1021/jacs.7b08064

Nickel: The “Spirited Horse” of Transition Metal Catalysis
journal, February 2015


Divergent Reactivity of a Dinuclear (NHC)Nickel(I) Catalyst versus Nickel(0) Enables Chemoselective Trifluoromethylselenolation
journal, September 2017

  • Dürr, Alexander B.; Fisher, Henry C.; Kalvet, Indrek
  • Angewandte Chemie International Edition, Vol. 56, Issue 43
  • DOI: 10.1002/anie.201706423

Theoretical Study on the Mechanism of Ni-Catalyzed Alkyl-Alkyl Suzuki Cross-Coupling
journal, February 2012

  • Li, Zhe; Jiang, Yuan-Ye; Fu, Yao
  • Chemistry - A European Journal, Vol. 18, Issue 14
  • DOI: 10.1002/chem.201103882

Mild, Safe, and Versatile Reagents for (CF 2 ) n Transfer and the Construction of Fluoroalkyl-Containing Rings
journal, November 2013

  • Kaplan, Peter T.; Xu, Long; Chen, Bo
  • Organometallics, Vol. 32, Issue 24
  • DOI: 10.1021/om401016k

Isolated Organometallic Nickel(III) and Nickel(IV) Complexes Relevant to Carbon–Carbon Bond Formation Reactions
journal, September 2016

  • Schultz, Jason W.; Fuchigami, Kei; Zheng, Bo
  • Journal of the American Chemical Society, Vol. 138, Issue 39
  • DOI: 10.1021/jacs.6b06862

Development of an Air-Stable Nickel Precatalyst for the Amination of Aryl Chlorides, Sulfamates, Mesylates, and Triflates
journal, November 2013

  • Park, Nathaniel H.; Teverovskiy, Georgiy; Buchwald, Stephen L.
  • Organic Letters, Vol. 16, Issue 1
  • DOI: 10.1021/ol403209k

Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation
journal, November 2014

  • Schley, Nathan D.; Fu, Gregory C.
  • Journal of the American Chemical Society, Vol. 136, Issue 47
  • DOI: 10.1021/ja508718m

Organometallic Nickel(III) Complexes Relevant to Cross-Coupling and Carbon–Heteroatom Bond Formation Reactions
journal, April 2014

  • Zheng, Bo; Tang, Fengzhi; Luo, Jia
  • Journal of the American Chemical Society, Vol. 136, Issue 17
  • DOI: 10.1021/ja5024749

Engaging Radicals in Transition Metal-Catalyzed Cross-Coupling with Alkyl Electrophiles: Recent Advances
journal, June 2017


Facile Access to Fluoromethylated Arenes by Nickel-Catalyzed Cross-Coupling between Arylboronic Acids and Fluoromethyl Bromide
journal, June 2015

  • An, Lun; Xiao, Yu-Lan; Min, Qiao-Qiao
  • Angewandte Chemie International Edition, Vol. 54, Issue 31
  • DOI: 10.1002/anie.201502882

Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium
journal, March 2017

  • Feng, Zhang; Min, Qiao-Qiao; Fu, Xia-Ping
  • Nature Chemistry, Vol. 9, Issue 9
  • DOI: 10.1038/nchem.2746

Photoredox-Catalysis-Modulated, Nickel-Catalyzed Divergent Difunctionalization of Ethylene
journal, January 2019


Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes
journal, January 2013

  • Standley, Eric A.; Jamison, Timothy F.
  • Journal of the American Chemical Society, Vol. 135, Issue 4
  • DOI: 10.1021/ja3116718

Ligand-Controlled Nickel-Catalyzed Reductive Relay Cross-Coupling of Alkyl Bromides and Aryl Bromides
journal, December 2017


Nickel-Catalyzed Kumada Cross-Coupling Reactions of Tertiary Alkylmagnesium Halides and Aryl Bromides/Triflates
journal, June 2011

  • Joshi-Pangu, Amruta; Wang, Chao-Yuan; Biscoe, Mark R.
  • Journal of the American Chemical Society, Vol. 133, Issue 22
  • DOI: 10.1021/ja202769t

Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis
journal, February 2016

  • Zuo, Zhiwei; Cong, Huan; Li, Wei
  • Journal of the American Chemical Society, Vol. 138, Issue 6
  • DOI: 10.1021/jacs.5b13211

A Five-Coordinate Nickel(II) Fluoroalkyl Complex as a Precursor to a Spectroscopically Detectable Ni(III) Species
journal, May 2013

  • Zhang, Cheng-Pan; Wang, Huan; Klein, Axel
  • Journal of the American Chemical Society, Vol. 135, Issue 22
  • DOI: 10.1021/ja4030462

Exploring Trifluoromethylation Reactions at Nickel: A Structural and Reactivity Study
journal, August 2008

  • Dubinina, Galyna G.; Brennessel, William W.; Miller, Jennifer L.
  • Organometallics, Vol. 27, Issue 15
  • DOI: 10.1021/om800300k

Preparation and properties of aryl(dipyridyl)nickel halide complexes
journal, January 1975


Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
journal, January 2010

  • Everson, Daniel A.; Shrestha, Ruja; Weix, Daniel J.
  • Journal of the American Chemical Society, Vol. 132, Issue 3
  • DOI: 10.1021/ja9093956

Transition-Metal Catalysis and Organocatalysis: Where Can Progress Be Expected?
journal, December 2015


The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis
journal, December 2001


A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters
journal, December 2016


Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction
journal, December 2018

  • Diccianni, Justin B.; Katigbak, Joseph; Hu, Chunhua
  • Journal of the American Chemical Society, Vol. 141, Issue 4
  • DOI: 10.1021/jacs.8b13499

Catalytic Dehydrogenative Cross-Coupling: Forming Carbon−Carbon Bonds by Oxidizing Two Carbon−Hydrogen Bonds
journal, March 2011

  • Yeung, Charles S.; Dong, Vy M.
  • Chemical Reviews, Vol. 111, Issue 3
  • DOI: 10.1021/cr100280d

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation
journal, May 2018

  • Sheng, Jie; Ni, Hui-Qi; Zhang, Hao-Ran
  • Angewandte Chemie International Edition, Vol. 57, Issue 26
  • DOI: 10.1002/anie.201803228

Understanding organofluorine chemistry. An introduction to the C–F bond
journal, January 2008