PMID: 11925243Apr 2, 2002Paper

Tuning of regioselectivity in the coupling reaction involving allenic/propargylic palladium species

The Journal of Organic Chemistry
Shengming Ma, Aibin Zhang

Abstract

Two different types of coupling patterns for the Pd(0)-catalyzed coupling reaction of allenic/propargylic zinc reagents with organic halides or propargylic carbonates (acetate) with the corresponding organometallic reagents were observed. After studying the controlling factors on the regioselectivity of this reaction, we demonstrated that the steric hindrance of both reactants and the types of organic halides determine the regioselectivity of this coupling reaction. By subtle choosing of the substrates, the regioselectivity can be tuned. On the basis of these results, new methodologies for the highly regio- and stereoselective synthesis of 6-substituted hex-5-yn-2-enoates and 4,6-dialkylhexa-2,4,5-trienoates have been developed. Some of the products synthesized by the carbonate protocol cannot be prepared by the lithiation protocol because the regioselectivity of lithiation of dialkyl-substituted internal alkynes is an intrinsic problem.

Citations

Jan 15, 2013·Tetrahedron·Ken S Feldman, Joshua F Antoline
Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Mar 5, 2014·Chemical Society Reviews·Benito AlcaideCristina Aragoncillo
Oct 28, 2015·Organic Letters·Charlotte A OsborneElizabeth R Jarvo
Sep 16, 2011·Angewandte Chemie·Katie M CergolMichael S Sherburn
Aug 30, 2018·Chemical Communications : Chem Comm·Junzhe XiaoShengming Ma
Mar 8, 2018·Antonie van Leeuwenhoek·Shaghayegh NasrSeyed Abolhassan Shahzadeh Fazeli
Apr 18, 2015·SpringerPlus·Md FakruddinMonzur Morshed Ahmed
Aug 1, 2007·Applied Microbiology and Biotechnology·Perng-Kuang ChangThomas E Cleveland
Mar 29, 2008·Microbial Ecology·A RodriguesF C Pagnocca
May 12, 2009·Environmental Monitoring and Assessment·Fatih Kalyoncu
Nov 26, 2013·The Journal of Organic Chemistry·Hanna M Wisniewska, Elizabeth R Jarvo
Aug 21, 2013·Journal of the American Chemical Society·Yang-Xiong LiChao-Jun Li
Aug 23, 2011·Organic Letters·Benjamin L Kohn, Elizabeth R Jarvo
Jan 31, 2020·Organic Letters·Peizhong XieTeck-Peng Loh
Feb 11, 2005·Journal of the American Chemical Society·Johan KjellgrenKálmán J Szabó
Oct 29, 2021·Chemical Communications : Chem Comm·Xue-Yi He, Zhong-Xia Wang

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