4.5 Article

Catalytic Availabilities of Lewis Acidic SnCl2: Ph3PAuCl-SnCl2 Composite Catalyzed Successive ortho-Alkenylation/O-Alkenylation of Phenols Followed by Cyclization to 1-Benzopyrans

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 34, Pages 5678-5685

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601042

Keywords

Homogeneous catalysis; Gold; Tin; Alkynes; Alkenylation; Cyclization

Funding

  1. Grants-in-Aid for Scientific Research [26410058] Funding Source: KAKEN

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A Ph3PAuCl-SnCl2 composite, prepared in situ from Ph3PAuCl and SnCl2, catalyzed the formation of 1-benzopyrans from phenols and phenylacetylene. The Ph3PAuCl-SnCl2 composite catalyzed reaction was presumed to proceed through the successive ortho-alkenylation and O-alkenylation of phenols with phenylacetylene followed by cyclization of the prepared ortho- and O-dialkenylated phenol derivatives. Conveniently, all reactions with Ph3PAuCl-SnCl2 composite were established without rigorous exclusion of air and water.

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