In:
Angewandte Chemie, Wiley, Vol. 130, No. 20 ( 2018-05-14), p. 5969-5972
Abstract:
We have developed a reductive carbonylation method by which unactivated alkyl iodides can be hydroxymethylated to provide one‐carbon‐extended alcohol products under Cu‐catalyzed conditions. The method is tolerant of alkyl β‐hydrogen atoms, is robust towards a wide variety of functional groups, and was applied to primary, secondary, and tertiary alkyl iodide substrates. Mechanistic experiments indicate that the transformation proceeds by atom‐transfer carbonylation (ATC) of the alkyl iodide followed in tandem by two CuH‐mediated reductions in rapid succession. This radical mechanism renders the Cu‐catalyzed system complementary to precious‐metal‐catalyzed reductive carbonylation reactions.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v130.20
DOI:
10.1002/ange.201801814
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
506609-8
detail.hit.zdb_id:
1479266-7