Regio- and stereoselective cross-coupling of tert-propargyl alcohols with bis(trimethylsilyl)acetylene and its utilization in constructing a fluorescent donor-acceptor system

Akinobu Horita; Hayato Tsurugi; Atsushi Funayama; Tetsuya Satoh; Masahiro Miura

doi:10.1021/ol070799k

Regio- and stereoselective cross-coupling of tert-propargyl alcohols with bis(trimethylsilyl)acetylene and its utilization in constructing a fluorescent donor-acceptor system

Org Lett. 2007 May 24;9(11):2231-3. doi: 10.1021/ol070799k. Epub 2007 May 4.

Authors

Akinobu Horita¹, Hayato Tsurugi, Atsushi Funayama, Tetsuya Satoh, Masahiro Miura

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 17477540
DOI: 10.1021/ol070799k

Abstract

1,1-Disubstituted 3-aryl-2-propyn-1-ols undergo regio- and stereoselective cross-coupling on treatment with bis(trimethylsilyl)acetylene in the presence of a rhodium catalyst via cleavage of C(sp)-C(sp3) and C(sp)-Si bonds to produce the corresponding 2-hydroxymethyl-(E)-enynes. The subsequent desilylative Sonogashira coupling followed by base-promoted cyclization affords fluorescent dihydrofuran derivatives.

Publication types

Research Support, Non-U.S. Gov't