4.7 Article

The Rh(II)-catalyzed formal N-S bond insertion reaction of aryldiazoacetates into N-phenyl-sulfenyl phthalimide

Journal

CHEMICAL COMMUNICATIONS
Volume 52, Issue 36, Pages 6079-6082

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc02641a

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Funding

  1. National Natural Science Foundation of China [81373303, 81473080, 81573299, 21502230]
  2. Jiangsu Province Natural Science Foundation [BK20150688]
  3. program for Changjiang Scholars and Innovative Research Team in University [IRT1193]

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The Rh(II)-catalyzed sulfur ylide [1,2]-rearrangement of carbenoids generated from aryldiazoacetates has been realized via N-S bond insertion, generating tertiary sulfides in moderate to excellent yields. This demonstrates the first use of the sulfur ylide [1,2]-rearrangement undergoing N-S bond insertion. This protocol could proceed smoothly with high regioselectivity, low catalyst loading (0.1 mol% Rh-2(OAc)(4)), gram-scale reaction and broad substrate scope. And the product could be converted into glycine derivatives through simple procedures.

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