Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles

Shrestha, Bijay; Basnet, Prakash; Dhungana, Roshan K.; KC, Shekhar; Thapa, Surendra; Sears, Jeremiah M.; Giri, Ramesh

doi:10.1021/jacs.7b06340

Title: Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles

Journal Article · 24 July 2017 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.7b06340 · OSTI ID:1399511

Shrestha, Bijay ^[1]; Basnet, Prakash ^[1]; Dhungana, Roshan K. ^[1]; KC, Shekhar ^[1]; Thapa, Surendra ^[1]; Sears, Jeremiah M. ^[2];

^[1]

Univ. of New Mexico, Albuquerque, NM (United States)
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

We disclose a strategy for Ni-catalyzed regioselective dicarbofunctionalization of olefins in styrene derivatives by intercepting Heck C(sp³)-NiX intermediates with arylzinc reagents. This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometallation, and stabilizing the Heck C(sp³)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps. This method affords diversely-substituted 1,1,2-riarylethyl products that occur as structural motifs in various natural products.

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Research Organization:: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1399511

Report Number(s):: SAND-2017-7180J; 655131

Journal Information:: Journal of the American Chemical Society, Vol. 139, Issue 31; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 158 works

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References (64)

Catalytic Asymmetric Tandem Transformations Triggered by Conjugate Additions Guo, Hong-Chao; Ma, Jun-An Angewandte Chemie International Edition, Vol. 45, Issue 3 https://doi.org/10.1002/anie.200500195	journal	January 2006
A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents Qin, T.; Cornella, J.; Li, C. Science, Vol. 352, Issue 6287 https://doi.org/10.1126/science.aaf6123	journal	April 2016
Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade Dhungana, Roshan K.; Shrestha, Bijay; Thapa-Magar, Rajani Organic Letters, Vol. 19, Issue 8 https://doi.org/10.1021/acs.orglett.7b00794	journal	April 2017
Cyclisations Involving Attack of Carbo- and Heteronucleophiles on Carbon-Carbon π-Bonds Activated by Organopalladium Complexes Balme, Geneviève; Bouyssi, Didier; Lomberget, Thierry Synthesis, Issue 14 https://doi.org/10.1055/s-2003-42082	journal	January 2003
Attaque nucleophile intramoleculaire d'organopalladiques issus de la carbopalladation d'alkylidenecyclopropanes. Fournet, Guy; Balme, Geneviève; Gore, Jacques Tetrahedron Letters, Vol. 28, Issue 39 https://doi.org/10.1016/S0040-4039(00)96556-0	journal	January 1987
Iron-Catalyzed Tandem Cyclization and Cross-Coupling Reactions of Iodoalkanes and Aryl Grignard Reagents: Iron-Catalyzed Tandem Cyclization and Cross-Coupling Reactions Kim, Jae Gon; Son, Young Hoon; Seo, Jin Won European Journal of Organic Chemistry, Vol. 2015, Issue 8 https://doi.org/10.1002/ejoc.201403511	journal	February 2015
Ni-Catalyzed Cascade Formation of C(sp3)C(sp3) Bonds by Cyclization and Cross-Coupling Reactions of Iodoalkanes with Alkyl Zinc Halides Phapale, Vilas B.; Buñuel, Elena; García-Iglesias, Miguel Angewandte Chemie International Edition, Vol. 46, Issue 46 https://doi.org/10.1002/anie.200702528	journal	November 2007
Iron-Catalyzed Chemoselective Cross-Coupling of Primary and Secondary Alkyl Halides with Arylzinc Reagents Nakamura, Masaharu; Ito, Shingo; Matsuo, Keiko Synlett, Issue 11 https://doi.org/10.1055/s-2005-871541	journal	January 2005
Cobalt-Catalyzed Tandem Radical Cyclization and Cross-Coupling Reaction: Its Application to Benzyl-Substituted Heterocycles Wakabayashi, Katsuyu; Yorimitsu, Hideki; Oshima, Koichiro Journal of the American Chemical Society, Vol. 123, Issue 22 https://doi.org/10.1021/ja0100423	journal	June 2001
Nickel-Mediated Inter- and Intramolecular Reductive Cross-Coupling of Unactivated Alkyl Bromides and Aryl Iodides at Room Temperature Yan, Chang-Song; Peng, Yu; Xu, Xiao-Bo Chemistry - A European Journal, Vol. 18, Issue 19 https://doi.org/10.1002/chem.201200190	journal	March 2012
Domino Carbopalladation–Cross-Coupling for the Synthesis of 3,3-Disubstituted Oxindoles Seashore-Ludlow, Brinton; Somfai, Peter Organic Letters, Vol. 14, Issue 15 https://doi.org/10.1021/ol301539p	journal	July 2012
Palladium catalysed tandem cyclisation-anion capture processes. Part 3. Organoboron anion transfer agents Grigg, Ronald; Sansano, JoséM.; Santhakumar, Vijayaratnam Tetrahedron, Vol. 53, Issue 34 https://doi.org/10.1016/S0040-4020(97)00754-0	journal	August 1997
Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling Thapa, Surendra; Basnet, Prakash; Giri, Ramesh Journal of the American Chemical Society, Vol. 139, Issue 16 https://doi.org/10.1021/jacs.7b01922	journal	April 2017
Catalytic Enantioselective Diarylation of Alkenes You, Wei; Brown, M. Kevin Journal of the American Chemical Society, Vol. 137, Issue 46 https://doi.org/10.1021/jacs.5b10176	journal	November 2015
Diarylation of Alkenes by a Cu-Catalyzed Migratory Insertion/Cross-Coupling Cascade You, Wei; Brown, M. Kevin Journal of the American Chemical Society, Vol. 136, Issue 42 https://doi.org/10.1021/ja509056j	journal	October 2014
Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles Cong, Huan; Fu, Gregory C. Journal of the American Chemical Society, Vol. 136, Issue 10 https://doi.org/10.1021/ja500706v	journal	February 2014
Chelation-Mediated Palladium(II)-Catalyzed Domino Heck−Mizoroki/Suzuki−Miyaura Reactions Using Arylboronic Acids: Increasing Scope and Mechanistic Understanding Yahiaoui, Samir; Fardost, Ashkan; Trejos, Alejandro The Journal of Organic Chemistry, Vol. 76, Issue 8 https://doi.org/10.1021/jo1018188	journal	March 2011
Palladium-Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen Urkalan, Kaveri Balan; Sigman, Matthew S. Angewandte Chemie International Edition, Vol. 48, Issue 17 https://doi.org/10.1002/anie.200900218	journal	April 2009
Development of Stereocontrolled Palladium(II)-Catalyzed Domino Heck/Suzuki β,α-Diarylation Reactions with Chelating Vinyl Ethers and Arylboronic Acids Trejos, Alejandro; Odell, Luke R.; Larhed, Mats ChemistryOpen, Vol. 1, Issue 1 https://doi.org/10.1002/open.201100010	journal	February 2012
Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides McMahon, Caitlin M.; Renn, Matthew S.; Alexanian, Erik J. Organic Letters, Vol. 18, Issue 16 https://doi.org/10.1021/acs.orglett.6b02154	journal	August 2016
Stereoselective Synthesis of Heterocyclic Zinc Reagents via a Nickel-Catalyzed Radical Cyclization Vaupel, Andrea; Knochel, Paul The Journal of Organic Chemistry, Vol. 61, Issue 17 https://doi.org/10.1021/jo960617s	journal	January 1996
Palladium-Catalyzed Cyclization/Carboalkoxylation of Alkenyl Indoles Liu, Cong; Widenhoefer, Ross A. Journal of the American Chemical Society, Vol. 126, Issue 33 https://doi.org/10.1021/ja046810i	journal	August 2004
Vicinal C-Functionalization of Alkenes. Pd/Light-Induced Multicomponent Coupling Reactions Leading to Functionalized Esters and Lactones Fusano, Akira; Sumino, Shuhei; Fukuyama, Takahide Organic Letters, Vol. 13, Issue 8 https://doi.org/10.1021/ol200536h	journal	April 2011
Domino Carbopalladation−Carbonylation: Generating Quaternary Stereocenters while Controlling β-Hydride Elimination Seashore-Ludlow, Brinton; Somfai, Peter Organic Letters, Vol. 12, Issue 17 https://doi.org/10.1021/ol1009703	journal	September 2010
Synthesis of ketones from iodoalkenes, carbon monoxide and 9-alkyl-9-borabicyclo[3.3.1]nonane derivatives via a radical cyclization and palladium-catalysed carbonylative cross-coupling sequence Ishiyama, Tatsuo; Murata, Miki; Suzuki, Akira Journal of the Chemical Society, Chemical Communications, Issue 3 https://doi.org/10.1039/c39950000295	journal	January 1995
Trapping σ-Alkyl-Palladium(II) Intermediates with Arynes Encompassing Intramolecular C−H Activation: Spirobiaryls through Pd-Catalyzed Cascade Reactions Pérez-Gómez, Marta; García-López, José-Antonio Angewandte Chemie International Edition, Vol. 55, Issue 46 https://doi.org/10.1002/anie.201607976	journal	October 2016
Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source Liu, Xianglei; Li, Bin; Gu, Zhenhua The Journal of Organic Chemistry, Vol. 80, Issue 15 https://doi.org/10.1021/acs.joc.5b01126	journal	July 2015
Recent fundamental studies on migratory insertion into metal-carbon bonds Cavell, Kingsley J. Coordination Chemistry Reviews, Vol. 155 https://doi.org/10.1016/S0010-8545(96)90182-4	journal	November 1996
Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds Iqbal, Javed; Bhatia, Beena; Nayyar, Naresh K. Chemical Reviews, Vol. 94, Issue 2 https://doi.org/10.1021/cr00026a008	journal	March 1994
A Palladium-Catalyzed Three-Component Cross-Coupling of Conjugated Dienes or Terminal Alkenes with Vinyl Triflates and Boronic Acids Liao, Longyan; Jana, Ranjan; Urkalan, Kaveri Balan Journal of the American Chemical Society, Vol. 133, Issue 15 https://doi.org/10.1021/ja201358b	journal	April 2011
Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction Wu, Xiang; Lin, Hua-Chen; Li, Ming-Li Journal of the American Chemical Society, Vol. 137, Issue 42 https://doi.org/10.1021/jacs.5b08734	journal	October 2015
Pd-Catalyzed Regioselective 1,2-Difunctionalization of Vinylarenes with Alkenyl Triflates and Aryl Boronic Acids at Ambient Temperature Kuang, Zhijie; Yang, Kai; Song, Qiuling Organic Letters, Vol. 19, Issue 10 https://doi.org/10.1021/acs.orglett.7b01036	journal	May 2017
Nickel-Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar-M (M=MgX, ZnX) Terao, Jun; Nii, Shinsuke; Chowdhury, Firoz A. Advanced Synthesis & Catalysis, Vol. 346, Issue 8 https://doi.org/10.1002/adsc.200404041	journal	July 2004
Cobalt-Catalyzed Three-Component Coupling Reaction of Alkyl Halides, 1,3-Dienes, and Trimethylsilylmethylmagnesium Chloride Mizutani, Keiya; Shinokubo, Hiroshi; Oshima, Koichiro Organic Letters, Vol. 5, Issue 21 https://doi.org/10.1021/ol0356643	journal	October 2003
Palladium-Catalyzed 1,1-Difunctionalization of Ethylene Saini, Vaneet; Sigman, Matthew S. Journal of the American Chemical Society, Vol. 134, Issue 28 https://doi.org/10.1021/ja304344h	journal	July 2012
Pd ^II -Catalyzed Oxidative 1,1-Diarylation of Terminal Olefins Werner, Erik W.; Urkalan, Kaveri B.; Sigman, Matthew S. Organic Letters, Vol. 12, Issue 12 https://doi.org/10.1021/ol1009575	journal	May 2010
Pd(0)-Catalyzed 1,1-Diarylation of Ethylene and Allylic Carbonates Saini, Vaneet; Liao, Longyan; Wang, Qiaofeng Organic Letters, Vol. 15, Issue 19 https://doi.org/10.1021/ol4023358	journal	September 2013
Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes García-Domínguez, Andrés; Li, Zhaodong; Nevado, Cristina Journal of the American Chemical Society, Vol. 139, Issue 20 https://doi.org/10.1021/jacs.7b03195	journal	May 2017
Copper-Catalyzed Cross-Coupling of Silicon Pronucleophiles with Unactivated Alkyl Electrophiles Coupled with Radical Cyclization Xue, Weichao; Qu, Zheng-Wang; Grimme, Stefan Journal of the American Chemical Society, Vol. 138, Issue 43 https://doi.org/10.1021/jacs.6b09596	journal	October 2016
Copper(I)-Catalyzed Stereo- and Chemoselective Borylative Radical Cyclization of Alkyl Halides Bearing an Alkene Moiety Iwamoto, Hiroaki; Akiyama, Sota; Hayama, Keiichi Organic Letters, Vol. 19, Issue 10 https://doi.org/10.1021/acs.orglett.7b00940	journal	May 2017
Tandem Difluoroalkylation-Arylation of Enamides Catalyzed by Nickel Gu, Ji-Wei; Min, Qiao-Qiao; Yu, Ling-Chao Angewandte Chemie International Edition, Vol. 55, Issue 40 https://doi.org/10.1002/anie.201606458	journal	September 2016
A Palladium-Catalyzed Three-Component-Coupling Strategy for the Differential Vicinal Diarylation of Terminal 1,3-Dienes Stokes, Benjamin J.; Liao, Longyan; de Andrade, Aline Mendes Organic Letters, Vol. 16, Issue 17 https://doi.org/10.1021/ol502279u	journal	August 2014
Thermal decomposition of bis(phosphine)platinum(II) metallocycles McDermott, Joseph X.; White, John F.; Whitesides, George M. Journal of the American Chemical Society, Vol. 98, Issue 21 https://doi.org/10.1021/ja00437a018	journal	October 1976
Enantioselective Synthesis of Six-Membered Palladacycles Having Metal-Bound Stereogenic Carbons: Isolation and Reactivity of Palladacycles Containing Readily Accessible β-Hydrogens Burke, Brenda J.; Overman, Larry E. Journal of the American Chemical Society, Vol. 126, Issue 51 https://doi.org/10.1021/ja045047p	journal	December 2004
On the Mechanism of the Palladium(II)-Catalyzed Decarboxylative Olefination of Arene Carboxylic Acids. Crystallographic Characterization of Non-Phosphine Palladium(II) Intermediates and Observation of Their Stepwise Transformation in Heck-like Processes Tanaka, Daisuke; Romeril, Stuart P.; Myers, Andrew G. Journal of the American Chemical Society, Vol. 127, Issue 29 https://doi.org/10.1021/ja052099l	journal	July 2005
β,γ-Vicinal Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Directed Nucleopalladation Liu, Zhen; Zeng, Tian; Yang, Kin S. Journal of the American Chemical Society, Vol. 138, Issue 46 https://doi.org/10.1021/jacs.6b09170	journal	November 2016
Asymmetric Palladium-Catalyzed Directed Intermolecular Fluoroarylation of Styrenes Talbot, Eric P. A.; Fernandes, Talita de A.; McKenna, Jeffrey M. Journal of the American Chemical Society, Vol. 136, Issue 11 https://doi.org/10.1021/ja412881j	journal	March 2014
Asymmetric Chiral Ligand-Directed Alkene Dioxygenation Neufeldt, Sharon R.; Sanford, Melanie S. Organic Letters, Vol. 15, Issue 1 https://doi.org/10.1021/ol303003g	journal	December 2012
Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins Matsubara, Ryosuke; Gutierrez, Alicia C.; Jamison, Timothy F. Journal of the American Chemical Society, Vol. 133, Issue 47 https://doi.org/10.1021/ja209235d	journal	November 2011
Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes Standley, Eric A.; Jamison, Timothy F. Journal of the American Chemical Society, Vol. 135, Issue 4 https://doi.org/10.1021/ja3116718	journal	January 2013
Nickel-Catalyzed Mizoroki-Heck Reaction of Aryl Sulfonates and Chlorides with Electronically Unbiased Terminal Olefins: High Selectivity for Branched Products Tasker, Sarah Z.; Gutierrez, Alicia C.; Jamison, Timothy F. Angewandte Chemie International Edition, Vol. 53, Issue 7 https://doi.org/10.1002/anie.201308391	journal	January 2014
Enantiospecific Intramolecular Heck Reactions of Secondary Benzylic Ethers Harris, Michael R.; Konev, Mikhail O.; Jarvo, Elizabeth R. Journal of the American Chemical Society, Vol. 136, Issue 22 https://doi.org/10.1021/ja5026485	journal	May 2014
Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary α-Carbonyl Alkyl Bromides Liu, Chao; Tang, Shan; Liu, Dong Angewandte Chemie International Edition, Vol. 51, Issue 15 https://doi.org/10.1002/anie.201108350	journal	March 2012
Condensation of organic bromides with vinyl compounds catalysed by nickel complexes in the presence of zinc Lebedev, S. A.; Lopatina, V. S.; Petrov, E. S. Journal of Organometallic Chemistry, Vol. 344, Issue 2 https://doi.org/10.1016/0022-328X(88)80484-4	journal	April 1988
Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins Gøgsig, Thomas M.; Kleimark, Jonatan; Nilsson Lill, Sten O. Journal of the American Chemical Society, Vol. 134, Issue 1 https://doi.org/10.1021/ja2084509	journal	December 2011
Stereoselective Heck arylation of a functionalized cyclopentenyl ether using (S)-N-methyl-pyrrolidine as the stereochemical controller Trejos, Alejandro; Sävmarker, Jonas; Schlummer, Stefanie Tetrahedron, Vol. 64, Issue 37 https://doi.org/10.1016/j.tet.2008.06.099	journal	September 2008
Oxygen Donor-Mediated Equilibration of Diastereomeric Alkene−Palladium(II) Intermediates in Enantioselective Desymmetrizing Heck Cyclizations Machotta, Axel B.; Straub, Bernd F.; Oestreich, Martin Journal of the American Chemical Society, Vol. 129, Issue 44 https://doi.org/10.1021/ja072571y	journal	November 2007
Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions Desrosiers, Jean-Nicolas; Hie, Liana; Biswas, Soumik Angewandte Chemie International Edition, Vol. 55, Issue 39 https://doi.org/10.1002/anie.201606955	journal	September 2016
Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups Tang, Jie; Hackenberger, Dagmar; Goossen, Lukas J. Angewandte Chemie International Edition, Vol. 55, Issue 37 https://doi.org/10.1002/anie.201605744	journal	August 2016
Stereoselective Synthesis of Multisubstituted Butadienes through Directed Mizoroki−Heck Reaction and Homocoupling Reaction of Vinyl(2-pyridyl)silane Itami, Kenichiro; Ushiogi, Yousuke; Nokami, Toshiki Organic Letters, Vol. 6, Issue 21 https://doi.org/10.1021/ol048620i	journal	October 2004
Highly Efficient Carbopalladation Across Vinylsilane: Dual Role of the 2-PyMe ₂ Si Group as a Directing Group and as a Phase Tag Itami, Kenichiro; Mitsudo, Koichi; Kamei, Toshiyuki Journal of the American Chemical Society, Vol. 122, Issue 48 https://doi.org/10.1021/ja002582q	journal	November 2000
Chelation-controlled, palladium-catalyzed vinylic substitution reactions of vinyl ethers. 2-Arylethanal equivalents from aryl halides Andersson, Carl Magnus; Larsson, Joakim; Hallberg, Anders The Journal of Organic Chemistry, Vol. 55, Issue 22 https://doi.org/10.1021/jo00309a020	journal	October 1990
Total Synthesis of Diverse Carbogenic Complexity within the Resveratrol Class from a Common Building Block Snyder, Scott A.; Breazzano, Steven P.; Ross, Audrey G. Journal of the American Chemical Society, Vol. 131, Issue 5 https://doi.org/10.1021/ja806183r	journal	January 2009
Identification of new triarylethylene oxyalkanoic acid analogues as bone selective estrogen mimetics Rubin, Valeria N.; Ruenitz, Peter C.; Boudinot, F. Douglas Bioorganic & Medicinal Chemistry, Vol. 9, Issue 6 https://doi.org/10.1016/S0968-0896(01)00038-4	journal	June 2001

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Nickel‐Catalyzed Asymmetric Reductive 1,2‐Carboamination of Unactivated Alkenes He, Jun; Xue, Yuhang; Han, Bo Angewandte Chemie, Vol. 132, Issue 6 https://doi.org/10.1002/ange.201913743	journal	December 2019
Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation Lv, Honggui; Kang, Huiying; Zhou, Biying Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-12949-1	journal	November 2019
Coordination Assisted Distal C−H Alkylation of Fused Heterocycles Ramakrishna, Kankanala; Biswas, Jyoti Prasad; Jana, Sadhan Angewandte Chemie, Vol. 131, Issue 39 https://doi.org/10.1002/ange.201907544	journal	July 2019
Alkylarylation of styrenes via direct C(sp ³ )–Br/C(sp ² )–H functionalization mediated by photoredox and copper cooperative catalysis Yong, Xin; Han, Ya-Fei; Li, Yang Chemical Communications, Vol. 54, Issue 91 https://doi.org/10.1039/c8cc07587e	journal	January 2018
Enantioselective palladium-catalyzed diarylation of unactivated alkenes Ju, Baihang; Chen, Shigui; Kong, Wangqing Chemical Communications, Vol. 55, Issue 95 https://doi.org/10.1039/c9cc07036b	journal	January 2019
Nickel‐Catalyzed 1,2‐Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3‐Trifunctionalized Building Blocks Derosa, Joseph; Kang, Taeho; Tran, Van T. Angewandte Chemie, Vol. 132, Issue 3 https://doi.org/10.1002/ange.201913062	journal	December 2019
Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents Chierchia, Matteo; Xu, Peilin; Lovinger, Gabriel J. Angewandte Chemie International Edition, Vol. 58, Issue 40 https://doi.org/10.1002/anie.201908029	journal	August 2019
Enantioselective Radical Addition/Cross‐Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents Chierchia, Matteo; Xu, Peilin; Lovinger, Gabriel J. Angewandte Chemie, Vol. 131, Issue 40 https://doi.org/10.1002/ange.201908029	journal	August 2019
Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay Zhao, Xian; Tu, Hai-Yong; Guo, Lei Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05951-6	journal	August 2018
H-bonded reusable template assisted para-selective ketonisation using soft electrophilic vinyl ethers Maji, Arun; Dahiya, Amit; Lu, Gang Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06018-2	journal	September 2018
Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation Lv, Honggui; Kang, Huiying; Zhou, Biying Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-12949-1	journal	November 2019
Intermolecular dialkylation of alkenes with two distinct C(sp ³ )─H bonds enabled by synergistic photoredox catalysis and iron catalysis Ouyang, Xuan-Hui; Li, Yang; Song, Ren-Jie Science Advances, Vol. 5, Issue 3 https://doi.org/10.1126/sciadv.aav9839	journal	March 2019