Issue 23, 2021

Rh(iii)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

Abstract

A Rh(III)-catalyzed tandem C(sp2)–H allylation/N-alkylation annulation reaction of arene amides employing 5-methylene-1,3-dioxan-2-one as an efficient allyl source has been disclosed for the first time, affording an unprecedented opportunity for the synthesis of 3,4-dihydropyrimido[1,6-a]indol-1(2H)-ones in moderate to excellent yields. Meanwhile, Rh(III)-catalyzed C(sp2)–H allylation products can also be obtained under altered reaction conditions. These practical and scalable divergent synthesis protocols proceeded smoothly under mild reaction conditions. Broad substrate scope, good functional group compatibility and total 32 examples were observed. Moreover, the preliminary mechanism studies show that the rhodium catalyst plays a dual role in the C–H activation and N-alkylation annulation process.

Graphical abstract: Rh(iii)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

Supplementary files

Article information

Article type
Research Article
Submitted
05 Aug 2021
Accepted
06 Oct 2021
First published
08 Oct 2021

Org. Chem. Front., 2021,8, 6585-6590

Rh(III)-Catalyzed tandem C(sp2)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates

H. Xie, J. Liang, Z. Huang, B. Shu, Y. Zheng, Y. Liu, S. Chen, X. Liu and S. Zhang, Org. Chem. Front., 2021, 8, 6585 DOI: 10.1039/D1QO01129D

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