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Transition Metal‐Free Aroylation of Diarylmethanes with N ‐Bn‐ N ‐Boc Arylamides and N ‐Acylpyrroles
Author(s) -
Yang Fan,
Zou Dong,
Chen Shuguang,
Wang Huan,
Zhao Yichen,
Zhao Liyi,
Li Linlin,
Li Jie,
Walsh Patrick J.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000622
Subject(s) - chemistry , transition metal , steric effects , reagent , amide , combinatorial chemistry , catalysis , cleavage (geology) , organic chemistry , geotechnical engineering , fracture (geology) , engineering
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 of N ‐Bn− N ‐Boc arylamides and N ‐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.