Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts

Basnet, Prakash; KC, Shekhar; Dhungana, Roshan K.; Shrestha, Bijay; Boyle, Timothy J.; Giri, Ramesh

doi:10.1021/jacs.8b09401

Title: Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts

Journal Article · 04 November 2018 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.8b09401 · OSTI ID:1485460

Basnet, Prakash ^[1]; KC, Shekhar ^[1]; Dhungana, Roshan K. ^[1]; Shrestha, Bijay ^[1];

^[2];

^[1]

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

Here, we disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective γ,δ-diarylation of unactivated alkenes in simple ketimines with aryl halides and arylzinc reagents. The bimetallic synergy, which generates cationic Ni(II) species during reaction, promotes migratory insertion and transmetalation steps and suppresses β-H elimination and cross-coupling, the major side reactions that cause serious problems during alkene difunctionalization. This diarylation reaction proceeds at remote locations to imines to afford, after simple H⁺ workup, diversely substituted γ,δ-diaryl ketones that are otherwise difficult to access readily with existing methods.

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

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

Grant/Contract Number:: AC04-94AL85000

OSTI ID:: 1485460

Report Number(s):: SAND--2018-12087J; 668982

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 46 Vol. 140; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (66)

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
Asymmetric Heck Reactions via Neutral Intermediates: Enhanced Enantioselectivity with Halide Additives Gives Mechanistic Insights Overman, Larry E.; Poon, Daniel J. Angewandte Chemie International Edition in English, Vol. 36, Issue 5 https://doi.org/10.1002/anie.199705181	journal	March 1997
Stille Coupling Made Easier—The Synergic Effect of Copper(I) Salts and the Fluoride Ion Mee, Simon P. H.; Lee, Victor; Baldwin, Jack E. Angewandte Chemie International Edition, Vol. 43, Issue 9 https://doi.org/10.1002/anie.200352979	journal	February 2004
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
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
Rhodium-Catalyzed Regioselective Carboacylation of Olefins: A CC Bond Activation Approach for Accessing Fused-Ring Systems Xu, Tao; Dong, Guangbin Angewandte Chemie International Edition, Vol. 51, Issue 30 https://doi.org/10.1002/anie.201202771	journal	June 2012
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
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
Stereospecific Palladium‐Catalyzed Acylation of Enantioenriched Alkylcarbastannatranes: A General Alternative to Asymmetric Enolate Reactions Wang, Chao‐Yuan; Ralph, Glenn; Derosa, Joseph Angewandte Chemie International Edition, Vol. 56, Issue 3 https://doi.org/10.1002/anie.201609930	journal	December 2016
Transition Metal-Catalyzed Dicarbofunctionalization of Unactivated Olefins Dhungana, Roshan K.; Kc, Shekhar; Basnet, Prakash The Chemical Record, Vol. 18, Issue 9 https://doi.org/10.1002/tcr.201700098	journal	March 2018
Reaction of diarylzinc compounds with copper(I) salts. Synthesis and characterization of arylcopper(I) compounds Hofstee, H. K.; Boersma, J.; Van Der Kerk, G. J. M. Journal of Organometallic Chemistry, Vol. 144, Issue 2 https://doi.org/10.1016/S0022-328X(00)84167-4	journal	January 1978
A new, easy synthesis of phenylsilver Boersma, J.; Des Tombe, F. J. A.; Weijers, F. Journal of Organometallic Chemistry, Vol. 124, Issue 2 https://doi.org/10.1016/S0022-328X(00)90970-7	journal	January 1977
Strategies toward Dicarbofunctionalization of Unactivated Olefins by Combined Heck Carbometalation and Cross-Coupling Giri, Ramesh; Kc, Shekhar The Journal of Organic Chemistry, Vol. 83, Issue 6 https://doi.org/10.1021/acs.joc.7b03128	journal	February 2018
Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products Kc, Shekhar; Basnet, Prakash; Thapa, Surendra The Journal of Organic Chemistry, Vol. 83, Issue 5 https://doi.org/10.1021/acs.joc.8b00184	journal	February 2018
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
Nickel-Catalyzed Reductive Conjugate Addition of Primary Alkyl Bromides to Enones To Form Silyl Enol Ethers Huihui, Kierra M. M.; Shrestha, Ruja; Weix, Daniel J. Organic Letters, Vol. 19, Issue 2 https://doi.org/10.1021/acs.orglett.6b03509	journal	January 2017
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
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
Palladium-catalyzed iodine-zinc exchange reactions. A new palladium-mediated intramolecular carbozincation of alkenes Stadtmueller, Heinz; Lentz, Ruth; Tucker, Charles E. Journal of the American Chemical Society, Vol. 115, Issue 15 https://doi.org/10.1021/ja00068a092	journal	July 1993
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
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
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
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
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
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
Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes McCammant, Matthew S.; Liao, Longyan; Sigman, Matthew S. Journal of the American Chemical Society, Vol. 135, Issue 11 https://doi.org/10.1021/ja3110544	journal	March 2013
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
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
Copper-Catalyzed Intermolecular Trifluoromethylarylation of Alkenes: Mutual Activation of Arylboronic Acid and CF ₃ ⁺ Reagent Wang, Fei; Wang, Dinghai; Mu, Xin Journal of the American Chemical Society, Vol. 136, Issue 29 https://doi.org/10.1021/ja504458j	journal	July 2014
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 Asymmetric Synthesis of Quaternary Carbon Centers. Exploratory Investigations of Intramolecular Heck Reactions of ( E )-α,β-Unsaturated 2-Haloanilides and Analogues To Form Enantioenriched Spirocyclic Products Ashimori, Atsuyuki; Bachand, Benoit; Overman, Larry E. Journal of the American Chemical Society, Vol. 120, Issue 26 https://doi.org/10.1021/ja980786p	journal	July 1998
Regioselective Double Alkylation of Styrenes with Alkyl Halides Using a Titanocene Catalyst Terao, Jun; Saito, Koyu; Nii, Shinsuke Journal of the American Chemical Society, Vol. 120, Issue 45 https://doi.org/10.1021/ja982732l	journal	November 1998
Iron-Catalyzed Olefin Carbometalation Nakamura, Masaharu; Hirai, Atsushi; Nakamura, Eiichi Journal of the American Chemical Society, Vol. 122, Issue 5 https://doi.org/10.1021/ja983066r	journal	January 2000
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
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
Enantioselective Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes via Radical Process Wang, Fei; Wang, Dinghai; Wan, Xiaolong Journal of the American Chemical Society, Vol. 138, Issue 48 https://doi.org/10.1021/jacs.6b10468	journal	November 2016
Asymmetric Cu-Catalyzed Intermolecular Trifluoromethylarylation of Styrenes: Enantioselective Arylation of Benzylic Radicals Wu, Lianqian; Wang, Fei; Wan, Xiaolong Journal of the American Chemical Society, Vol. 139, Issue 8 https://doi.org/10.1021/jacs.6b13299	journal	February 2017
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
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
Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation Walker, James A.; Vickerman, Kevin L.; Humke, Jenna N. Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b06191	journal	July 2017
Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles Shrestha, Bijay; Basnet, Prakash; Dhungana, Roshan K. Journal of the American Chemical Society, Vol. 139, Issue 31 https://doi.org/10.1021/jacs.7b06340	journal	July 2017
Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling Derosa, Joseph; Tran, Van T.; Boulous, Mark N. Journal of the American Chemical Society, Vol. 139, Issue 31 https://doi.org/10.1021/jacs.7b06567	journal	July 2017
“Cationic” Suzuki–Miyaura Coupling with Acutely Base-Sensitive Boronic Acids Chen, Liye; Sanchez, Daniel R.; Zhang, Bufan Journal of the American Chemical Society, Vol. 139, Issue 36 https://doi.org/10.1021/jacs.7b07687	journal	September 2017
Ni-Catalyzed Regioselective β,δ-Diarylation of Unactivated Olefins in Ketimines via Ligand-Enabled Contraction of Transient Nickellacycles: Rapid Access to Remotely Diarylated Ketones Basnet, Prakash; Dhungana, Roshan K.; Thapa, Surendra Journal of the American Chemical Society, Vol. 140, Issue 25 https://doi.org/10.1021/jacs.8b03163	journal	May 2018
Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp ³ )–C(sp ³ )/C(sp ³ )–C(sp ² ) Bond Formation and Mechanistic Studies Kc, Shekhar; Dhungana, Roshan K.; Shrestha, Bijay Journal of the American Chemical Society, Vol. 140, Issue 31 https://doi.org/10.1021/jacs.8b05374	journal	July 2018
Nickel-Catalyzed Stereoselective Diarylation of Alkenylarenes Gao, Pin; Chen, Liang-An; Brown, M. Kevin Journal of the American Chemical Society, Vol. 140, Issue 34 https://doi.org/10.1021/jacs.8b05680	journal	July 2018
Enantioselective Trifluoromethylalkynylation of Alkenes via Copper-Catalyzed Radical Relay Fu, Liang; Zhou, Song; Wan, Xiaolong Journal of the American Chemical Society, Vol. 140, Issue 35 https://doi.org/10.1021/jacs.8b07436	journal	August 2018
1,10-Phenanthroline derivatives: a new ligand class in the Heck reaction. Mechanistic aspects Cabri, Walter; Candiani, Ilaria; Bedeschi, Angelo The Journal of Organic Chemistry, Vol. 58, Issue 26 https://doi.org/10.1021/jo00078a021	journal	December 1993
On the Nature of the "Copper Effect" in the Stille Cross-Coupling Farina, Vittorio; Kapadia, Suresh; Krishnan, Bala The Journal of Organic Chemistry, Vol. 59, Issue 20 https://doi.org/10.1021/jo00099a018	journal	October 1994
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
Copper-Mediated Cyanotrifluoromethylation of Styrenes Using the Togni Reagent Ilchenko, Nadia O.; Janson, Pär G.; Szabó, Kálmán J. The Journal of Organic Chemistry, Vol. 78, Issue 21 https://doi.org/10.1021/jo401831t	journal	October 2013
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
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
Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes He, Yu-Tao; Li, Lian-Hua; Yang, Yan-Fang Organic Letters, Vol. 16, Issue 1 https://doi.org/10.1021/ol403263c	journal	December 2013
Cyclization of Dinuclear Aryl- and Aroylpalladium Complexes with the Metal Centers Tethered by an Oligo(ethylene oxide) Chain. Intramolecular Transmetalation of the Cationic Dinuclear Arylpalladium Complexes Suzaki, Yuji; Osakada, Kohtaro Organometallics, Vol. 22, Issue 11 https://doi.org/10.1021/om030035i	journal	May 2003
Development and investigation of a site selective palladium-catalyzed 1,4-difunctionalization of isoprene using pyridine–oxazoline ligands McCammant, Matthew S.; Sigman, Matthew S. Chemical Science, Vol. 6, Issue 2 https://doi.org/10.1039/C4SC03074E	journal	January 2015
Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction Maity, Soham; Dolui, Pravas; Kancherla, Rajesh Chemical Science, Vol. 8, Issue 7 https://doi.org/10.1039/C7SC01204G	journal	January 2017
Nickel-catalyzed difunctionalization of allyl moieties using organoboronic acids and halides with divergent regioselectivities Li, Wanfang; Boon, Jie Kang; Zhao, Yu Chemical Science, Vol. 9, Issue 3 https://doi.org/10.1039/C7SC03149A	journal	January 2018
Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles Thapa, Surendra; Dhungana, Roshan K.; Magar, Rajani Thapa Chemical Science, Vol. 9, Issue 4 https://doi.org/10.1039/C7SC04351A	journal	January 2018
Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis Xiao, Jian; Cong, Xiao-Wei; Yang, Gui-Zhen Chemical Communications, Vol. 54, Issue 16 https://doi.org/10.1039/C8CC00001H	journal	January 2018
Ni-catalyzed two-component reductive dicarbofunctionalization of alkenes via radical cyclization Kuang, Yulong; Wang, Xuefeng; Anthony, David Chemical Communications, Vol. 54, Issue 20 https://doi.org/10.1039/C8CC00358K	journal	January 2018
Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds Derosa, Joseph; van der Puyl, Vincent A.; Tran, Van T. Chemical Science, Vol. 9, Issue 23 https://doi.org/10.1039/C8SC01735B	journal	January 2018
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
Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement Zhang, L.; Lovinger, G. J.; Edelstein, E. K. Science, Vol. 351, Issue 6268 https://doi.org/10.1126/science.aad6080	journal	December 2015
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

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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

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