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Rh(III)-catalyzed regioselective intermolecular N-methylene Csp3–H bond carbenoid insertion

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Abstract

A Rh(III)-catalyzed regioselective intermolecular carbenoid insertion into the N-methylene Csp3–H bond of acyclic aliphatic amides has been achieved, taking advantage of bidentate–chelation assistance. This methodology has been successfully applied to a broad range of linear and branched-chain N-alkylamides, thus providing a practical method for the assembly of diverse beta-amino esters. Mechanism studies and density functional theory (DFT) calculations revealed that a singlet Fischer type carbene insertion via an outer-sphere pathway was involved in this N-methylene Csp3–H bond carbenoid insertion.

Graphical abstract: Rh(iii)-catalyzed regioselective intermolecular N-methylene Csp3–H bond carbenoid insertion

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Publication details

The article was received on 31 Aug 2017, accepted on 26 Nov 2017 and first published on 27 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC03802J
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Rh(III)-catalyzed regioselective intermolecular N-methylene Csp3–H bond carbenoid insertion

    H. Xie, Z. Ye, Z. Ke, J. Lan, H. Jiang and W. Zeng, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC03802J

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