Cobalt-catalyzed intermolecular hydroacylation of olefins through chelation-assisted imidoyl C-H activation

A low-valent cobalt catalyst generated from cobalt(II) bromide, a diphosphine ligand, and zinc powder promotes intermolecular hydroacylation of olefins using N-3-picolin-2-yl aldimines as aldehyde equivalents, which affords, upon acidic hydrolysis, ketone products in moderate to good yields with hig...

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Bibliographic Details
Main Authors: Yang, Junfeng, Seto, Yuan Wah, Yoshikai, Naohiko
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2015
Subjects:
Online Access:https://hdl.handle.net/10356/79348
http://hdl.handle.net/10220/38495
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Institution: Nanyang Technological University
Language: English
Description
Summary:A low-valent cobalt catalyst generated from cobalt(II) bromide, a diphosphine ligand, and zinc powder promotes intermolecular hydroacylation of olefins using N-3-picolin-2-yl aldimines as aldehyde equivalents, which affords, upon acidic hydrolysis, ketone products in moderate to good yields with high linear selectivity. The reaction is applicable to styrenes, vinylsilanes, and aliphatic olefins as well as to various aryl and heteroaryl aldimines. The cobalt catalysis features a distinctively lower reaction temperature (60 °C) compared with those required for the same type of transformations catalyzed by rhodium complexes (typically 130–150 °C).