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C-Alkylation of N-alkylamides with styrenes in air and scale-up using a microwave flow reactor.

Authors :
Barham JP
Tamaoki S
Egami H
Ohneda N
Okamoto T
Odajima H
Hamashima Y
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2018 Nov 07; Vol. 16 (41), pp. 7568-7573. Date of Electronic Publication: 2018 Oct 09.
Publication Year :
2018

Abstract

C-Alkylation of N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to 65 g h <superscript>-1</superscript> product) was demonstrated using a Microwave Flow reactor, as the first example of a C-alkylation reaction using styrenes in continuous flow.

Details

Language :
English
ISSN :
1477-0539
Volume :
16
Issue :
41
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
30298895
Full Text :
https://doi.org/10.1039/c8ob02282h