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Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
Author(s) -
Ruzi Rehanguli,
Ma Junyang,
Yuan XiangAi,
Wang Wenliang,
Wang Shanshan,
Zhang Muliang,
Dai Jie,
Xie Jin,
Zhu Chengjian
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903816
Subject(s) - chemistry , substituent , aryl , bond cleavage , redox , combinatorial chemistry , substrate (aquarium) , catalysis , photoredox catalysis , stereochemistry , organic chemistry , photocatalysis , alkyl , oceanography , geology
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C−O bond and formation of a weaker C−C bond by 1,5‐aryl migration under mild reaction conditions. This new protocol is independent of substrate redox‐potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o ‐amino and o ‐hydroxy diaryl ketones under redox‐neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)‐yaequinolone A2, and a viridicatin derivative in satisfying yields.