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Cobalt(III)‐Catalyzed Alkylation of Primary C( sp 3 )–H Bonds with Diazo Compounds
Author(s) -
Yan ShengYi,
Ling PengXiang,
Shi BingFeng
Publication year - 2017
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.201700636
Subject(s) - carbenoid , chemistry , diazo , metalation , alkylation , insertion reaction , carbene , cobalt , catalysis , medicinal chemistry , cyclopropanation , chelation , hydroamination , combinatorial chemistry , stereochemistry , organic chemistry , rhodium
Chelation‐assisted C( sp 2 )–H metalation/carbenoid insertion has been well investigated. However, the analogous carbene functionalization of C( sp 3 )–H bonds remains a great challenge. Here we report the first cobalt(III)‐catalyzed alkylation of 8‐methylquinolines with diazo compounds through primary C( sp 3 )–H cobaltation/carbenoid insertion. The reaction is highly efficient, scalable and tolerates a variety of functional groups. Furthermore, the unique protocol can be applied to the synthesis of azatricyclic antibiotic compounds.