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Org Biomol Chem. 2018 Nov 7;16(41):7568-7573. doi: 10.1039/c8ob02282h. Epub 2018 Oct 9.

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

Author information

1
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan. hamashima@u-shizuoka-ken.ac.jp and SAIDA FDS INC. 143-10, Isshiki, Yaizu, Shizuoka, 425-0054, Japan. j.barham@saidagroup.jp.
2
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan. hamashima@u-shizuoka-ken.ac.jp.
3
SAIDA FDS INC. 143-10, Isshiki, Yaizu, Shizuoka, 425-0054, Japan. j.barham@saidagroup.jp.

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-1 product) was demonstrated using a Microwave Flow reactor, as the first example of a C-alkylation reaction using styrenes in continuous flow.

PMID:
30298895
DOI:
10.1039/c8ob02282h

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