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Title: Transition Metal‐Free Aroylation of Diarylmethanes with N ‐Bn‐ N ‐Boc Arylamides and N ‐Acylpyrroles
Abstract

In the last 20 years, efficient transition metal catalysts for the α‐arylation of enolates have been introduced. Despite the popularity and utility of these reactions, there remains room for improvement (reduced costs, elimination of transition metals and specialized ligands). Herein is reported a general, scalable and green method for aroylation of simple diarylmethane pronucleophiles through direct acyl C−N cleavage ofN‐Bn−N‐Boc arylamides andN‐acylpyrroles under transition metal‐free conditions. Importantly, a 1 : 1 ratio of the amide to the pronucleophile is employed. Unlike use of Weinreb amides, this method avoids preformed organometallics (organolithium and Grignard reagents) and does not employ cryogenic temperatures, which are difficult and costly to achieve on scale. The operationally simple protocol provides straightforward access to a variety of sterically and electronically diverse 1,2,2‐triarylethanones, a group of compounds with high‐value in medicinal chemistry.

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Award ID(s):
1902509
NSF-PAR ID:
10175067
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Advanced Synthesis & Catalysis
Volume:
362
Issue:
16
ISSN:
1615-4150
Page Range / eLocation ID:
p. 3423-3430
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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