钯催化炔烃的立体专一性脱羧苄基化反应

Palladium-Catalyzed Stereospecific Decarboxylative Benzylation of Alkynes.

作者信息

Mendis Shehani N, Tunge Jon A

机构信息

Department of Chemistry, The University of Kansas , 2010 Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.

出版信息

Org Lett. 2015 Nov 6;17(21):5164-7. doi: 10.1021/acs.orglett.5b02410. Epub 2015 Oct 9.

DOI:10.1021/acs.orglett.5b02410

PMID:26450113

Abstract

Enantioenriched benzyl esters of propiolic acids undergo highly stereospecific decarboxylative coupling to provide 1,1-diarylethynyl methanes. This sp-sp(3) coupling does not require strongly basic conditions or preformed organometallics and produces CO2 as the sole byproduct. Ultimately, this method results in the successful transfer of stereochemical information from secondary benzyl alcohols to generate enantioenriched tertiary diarylmethanes.

摘要

丙炔酸的对映体富集苄酯会发生高度立体专一性的脱羧偶联反应，生成1,1 - 二芳基乙炔基甲烷。这种sp-sp³偶联反应不需要强碱条件或预制的有机金属化合物，并且仅产生二氧化碳作为副产物。最终，该方法成功地将立体化学信息从仲苄醇转移，生成对映体富集的叔二芳基甲烷。