Issue 7, 2016

Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes

Abstract

Products obtained from palladium-catalyzed regioselective cis-addition of (chlorodimethylsilyl)pinacolborane to the alkyne bond of 1,4-disubstituted 1,3-enynes were subjected to Suzuki–Miyaura coupling with alkenyl iodides. Hiyama coupling of the resulting silanol-functionalized trienes provided tetrasubstituted conjugated trienes with different substitution patterns, whereas protiodesilylation with fluoride gave trisubstituted trienes. The methodology presented gives access to conjugated trienes with control of regio- and stereochemistry.

Graphical abstract: Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes

Supplementary files

Article information

Article type
Paper
Submitted
01 Apr 2016
Accepted
17 May 2016
First published
18 May 2016

New J. Chem., 2016,40, 6340-6346

Regio- and stereoselective synthesis of conjugated trienes from silaborated 1,3-enynes

E. Li, H. Zhou, V. Östlund, R. Hertzberg and C. Moberg, New J. Chem., 2016, 40, 6340 DOI: 10.1039/C6NJ01019A

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