Convenient Synthesis of Allylic Sulfides and Application to Allylic Carbon-Carbon Bond Formation

Kanoko TSUBOYAMA; Kazuyoshi TAKEDA; Katsumi TORII; Haruo OGURA

doi:10.1248/cpb.38.2357

Kanoko TSUBOYAMA, Kazuyoshi TAKEDA, Katsumi TORII, Haruo OGURA

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Keywords: S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate, carbon-carbon bond formation, cross-coupling reaction, allylic sulfide, copper(I) bromide, palladium(0)

JOURNAL FREE ACCESS

1990 Volume 38 Issue 9 Pages 2357-2363

DOI https://doi.org/10.1248/cpb.38.2357

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Abstract

Allylic sulfides were synthesized from allylic alcohols 1 using S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (2) by means of a single-step reaction. The allylic sulfides were coupled with a Grignard reagent or carbanion in the presence of a catalytic amount of copper(I) bromide or palladium(0).

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