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
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 inser...
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Published in | Journal of the American Chemical Society Vol. 140; no. 46; pp. 15586 - 15590 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
21.11.2018
Amer Chemical Soc American Chemical Society (ACS) |
Subjects | |
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Abstract | 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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AbstractList | 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. 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. 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. We disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective ykdiarylation 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 beta-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 gamma,delta-diaryl ketones that are otherwise difficult to access readily with existing methods. 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. |
Author | Dhungana, Roshan K KC, Shekhar Shrestha, Bijay Giri, Ramesh Boyle, Timothy J Basnet, Prakash |
AuthorAffiliation | Advanced Materials Laboratory Department of Chemistry & Chemical Biology Sandia National Laboratory |
AuthorAffiliation_xml | – name: Department of Chemistry & Chemical Biology – name: Sandia National Laboratory – name: Advanced Materials Laboratory |
Author_xml | – sequence: 1 givenname: Prakash surname: Basnet fullname: Basnet, Prakash organization: Department of Chemistry & Chemical Biology – sequence: 2 givenname: Shekhar surname: KC fullname: KC, Shekhar organization: Department of Chemistry & Chemical Biology – sequence: 3 givenname: Roshan K surname: Dhungana fullname: Dhungana, Roshan K organization: Department of Chemistry & Chemical Biology – sequence: 4 givenname: Bijay surname: Shrestha fullname: Shrestha, Bijay organization: Department of Chemistry & Chemical Biology – sequence: 5 givenname: Timothy J orcidid: 0000-0002-1251-5592 surname: Boyle fullname: Boyle, Timothy J organization: Advanced Materials Laboratory – sequence: 6 givenname: Ramesh orcidid: 0000-0002-8993-9131 surname: Giri fullname: Giri, Ramesh email: rgiri@unm.edu organization: Department of Chemistry & Chemical Biology |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30392352$$D View this record in MEDLINE/PubMed https://www.osti.gov/servlets/purl/1485460$$D View this record in Osti.gov |
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Keywords | PALLADIUM 3-COMPONENT COUPLING REACTION UNACTIVATED OLEFINS DICARBOFUNCTIONALIZATION INTRAMOLECULAR HECK REACTIONS COPPER(I) SALTS TERMINAL ALKENES CYCLIZATION ALKYL-HALIDES INTERMOLECULAR CYANOTRIFLUOROMETHYLATION |
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Snippet | We disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective γ,δ-diarylation of unactivated alkenes in simple ketimines with... We disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective ykdiarylation of unactivated alkenes in simple ketimines with... Here, we disclose unprecedented synergistic bimetallic Ni/Ag and Ni/Cu catalysts for regioselective γ,δ-diarylation of unactivated alkenes in simple ketimines... |
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SubjectTerms | Chemistry Chemistry, Multidisciplinary INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Physical Sciences Science & Technology |
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 |
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