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

CHEMICAL SOCIETY REVIEWS (2014)

期刊

CHEMICAL SOCIETY REVIEWS

卷 43, 期 15, 页码 5151-5162

出版社

ROYAL SOC CHEMISTRY

DOI: 10.1039/c4cs00072b

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Chemistry, Multidisciplinary

资金

National Science Foundation [CHE 1213246]
Division Of Chemistry
Direct For Mathematical & Physical Scien [1213246] Funding Source: National Science Foundation

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摘要

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.

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