Palladium-Catalyzed Alkynylation of Morita-Baylis-Hillman Carbonates with (Triisopropylsilyl)acetylene on Water

Yangxiong Li; Li Liu; Delong Kong; Dong Wang; Weichun Feng; Tao Yue; Chaojun Li

doi:10.1021/acs.joc.5b00728

Palladium-Catalyzed Alkynylation of Morita-Baylis-Hillman Carbonates with (Triisopropylsilyl)acetylene on Water

J Org Chem. 2015 Jun 19;80(12):6283-90. doi: 10.1021/acs.joc.5b00728. Epub 2015 Jun 1.

Authors

Yangxiong Li¹, Li Liu¹, Delong Kong¹, Dong Wang¹, Weichun Feng², Tao Yue², Chaojun Li³

Affiliations

¹ †Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
² §Chemical Technology Academy of Shandong Province, Jinan 250014, China.
³ ‡Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 0B8.

PMID: 25989102
DOI: 10.1021/acs.joc.5b00728

Abstract

Direct alkynylation of Morita-Baylis-Hillman carbonates with (triisopropylsilyl)acetylene catalyzed by a Pd(OAc)2-NHC complex was developed "on water" to give the corresponding 1,4-enynes. The significant effects of water amount in the solvent on further transformations of 1,4-enynes were investigated.