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Mn I /Ag I Relay Catalysis: Traceless Diazo‐Assisted C(sp 2 )–H/C(sp 3 )–H Coupling to β‐(Hetero)Aryl/Alkenyl Ketones
Author(s) -
Lu Qingquan,
Mondal Shobhan,
Cembellín Sara,
Glorius Frank
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201803384
Subject(s) - diazo , aryl , carbene , chemistry , regioselectivity , catalysis , medicinal chemistry , organic chemistry , alkyl
An unprecedented Mn I /Ag I ‐relay‐catalyzed C(sp 2 )−H/C(sp 3 )−H coupling of (vinyl)arenes with α‐diazoketones is reported, wherein the diazo group was exploited as a traceless auxiliary for control of regioselectivity. Challenging β‐(hetero)aryl/alkenyl ketones were obtained through this operationally simple approach. The cascade process merges denitrogenation, carbene rearrangement, C−H activation, and hydroarylation/hydroalkenylation. The robustness of this method was demonstrated at preparative scale and applied to late‐stage diversification of natural products.