4.5 Article

Cross-Coupling of N-Allylic Sulfonimides with Organozinc Reagents at Room Temperature

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 22, Pages 4107-4109

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200594

Keywords

Sulfur; Alkenes; Cross-coupling; Zinc; Palladium

Funding

  1. National Natural Science Foundation of China [21172206, 21072180, 20972147, J1030412]
  2. National Basic Research Program of China (973 Program) [2010CB833300]
  3. Program for Changjiang Scholars and Innovative Research Team in University [IRT1189]

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An efficient cross-coupling reaction of N-allylic sulfonimides with organozinc reagents has been developed. In the presence of 1 mol-% of Pd2(dba)3, a range of N-allylic sulfonimides smoothly couple with various organozinc reagents at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive a-selectivity. It is noteworthy that allyl ether, benzyl ether, and ester are tolerated under the reaction conditions.

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