Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic control vs. kinetic control of N,N-Boc2-amides-Reference-Cited by-同舟云学术

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic control vs. kinetic control of N,N-Boc2-amides

Published:2020 Issue:20 Volume:18 Page:3827-3831
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Li Guangchen¹²³⁴^ORCID,Szostak Michal¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. Rutgers University

3. Newark

4. USA

Abstract

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents after Mg/halide exchange with i-PrMgCl·LiCl is reported.

Funder

National Science Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB00813C

Reference75 articles.

1. Increasing the Reactivity of Amides towards Organometallic Reagents: An Overview

2. Computational studies on Ni-catalyzed amide C–N bond activation

3. B. M. Trost and I.Fleming , Comprehensive Organic Synthesis , Pergamon Press , 1991

4. M. B. Smith and J.March , Advanced Organic Chemistry , Wiley , 2007

5. A. Greenberg , C. M.Breneman and J. F.Liebman , The Amide Linkage: Structural Significance in Chemistry , Biochemistry and Materials Science , Wiley , 2003

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