skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Abstract

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.

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]
  1. The Univ. of New Mexico, Albuquerque, NM (United States)
  2. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Publication Date:
Research Org.:
Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA)
OSTI Identifier:
1485460
Report Number(s):
SAND-2018-12087J
Journal ID: ISSN 0002-7863; 668982
Grant/Contract Number:  
AC04-94AL85000
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 140; Journal Issue: 46; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Basnet, Prakash, KC, Shekhar, Dhungana, Roshan K., Shrestha, Bijay, Boyle, Timothy J., and Giri, Ramesh. 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. United States: N. p., 2018. Web. doi:10.1021/jacs.8b09401.
Basnet, Prakash, KC, Shekhar, Dhungana, Roshan K., Shrestha, Bijay, Boyle, Timothy J., & Giri, Ramesh. 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. United States. doi:10.1021/jacs.8b09401.
Basnet, Prakash, KC, Shekhar, Dhungana, Roshan K., Shrestha, Bijay, Boyle, Timothy J., and Giri, Ramesh. Mon . "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". United States. doi:10.1021/jacs.8b09401.
@article{osti_1485460,
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},
author = {Basnet, Prakash and KC, Shekhar and Dhungana, Roshan K. and Shrestha, Bijay and Boyle, Timothy J. and Giri, Ramesh},
abstractNote = {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.},
doi = {10.1021/jacs.8b09401},
journal = {Journal of the American Chemical Society},
issn = {0002-7863},
number = 46,
volume = 140,
place = {United States},
year = {2018},
month = {11}
}

Journal Article:
Free Publicly Available Full Text
This content will become publicly available on November 5, 2019
Publisher's Version of Record

Save / Share: