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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]
+ Show Author Affiliations
  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:
Research Org.:
Lehigh Univ., Bethlehem, PA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC); Science & Technology Department of Sichuan Province; Key Laboratory of Vanadium and Titanium of Sichuan Province; Sichuan University of Science and Engineering
OSTI Identifier:
1509518
Alternate Identifier(s):
OSTI ID: 1611202; OSTI ID: 1696921
Grant/Contract Number:  
SC0009363; 12502131; 21672096; 21702095; 2018JZ0061; 2018HH0128; 18CZ0024; 2108FTSZ03; 2017RCL03
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
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; chemistry

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.
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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. https://doi.org/10.1039/C9SC00554D
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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. https://doi.org/10.1039/C9SC00554D.
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@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}
}
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https://doi.org/10.1039/C9SC00554D
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  • 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
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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

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, Vol. 127, Issue 45
  • DOI: 10.1002/ange.201505699

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

  • Ruan, Zhixiong; Lackner, Sebastian; Ackermann, Lutz
  • Angewandte Chemie, Vol. 128, Issue 9
  • DOI: 10.1002/ange.201510743

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

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, Vol. 126, Issue 29
  • DOI: 10.1002/ange.201402695

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, Vol. 129, Issue 43
  • DOI: 10.1002/ange.201706423
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    Nickel‐Catalyzed Reductive Coupling for Transforming Unactivated Aryl Electrophiles into β‐Fluoroethylarenes
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    • Takahashi, Rina; Kubota, Koji; Ito, Hajime
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    • DOI: 10.1039/c9cc06946a
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