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Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

ABSTRACT: Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form ?,?-unsaturated thiocarbenium ions through oxidative carbon-hydrogen bond cleavage. These electrophiles couple with appended ?-nucleophiles to yield sulfur-containing heterocycles through carbon-carbon bond formation. Several nucleophiles are compatible with the procedure, and the reactions generally proceed through readily predictable transition states.

SUBMITTER: Cui Y

PROVIDER: S-EPMC3321134 | biostudies-literature | 2012 Apr

REPOSITORIES: biostudies-literature

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Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Cui Yubo Y Floreancig Paul E PE

Organic letters 20120315 7

Vinyl sulfides react rapidly and efficiently with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form α,β-unsaturated thiocarbenium ions through oxidative carbon-hydrogen bond cleavage. These electrophiles couple with appended π-nucleophiles to yield sulfur-containing heterocycles through carbon-carbon bond formation. Several nucleophiles are compatible with the procedure, and the reactions generally proceed through readily predictable transition states. ...[more]

PMID: 22420412

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