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Issue 15, 2014
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Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

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Abstract

Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N-sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. These intermediates undergo a variety of synthetically useful transformations, which include transannulation reactions to generate new heterocycles, cyclopropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C–H functionalization. Furthermore, many of these transformations can be conducted with high levels of enantioselectivity by use of chiral rhodium(II) catalysts.

Graphical abstract: Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

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Article information


Submitted
08 Feb 2014
First published
07 May 2014

Chem. Soc. Rev., 2014,43, 5151-5162
Article type
Tutorial Review

Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

H. M. L. Davies and J. S. Alford, Chem. Soc. Rev., 2014, 43, 5151 DOI: 10.1039/C4CS00072B

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