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

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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.

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

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Publication details

The article was received on 15 Sep 2018, accepted on 28 Sep 2018 and first published on 29 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB02282H
Citation: Org. Biomol. Chem., 2018, Advance Article
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    C-Alkylation of N-alkylamides with styrenes in air and scale-up using a microwave flow reactor

    J. P. Barham, S. Tamaoki, H. Egami, N. Ohneda, T. Okamoto, H. Odajima and Y. Hamashima, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02282H

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