One-pot synthesis of 1,3-disubstituted allenes from 1-alkynes, aldehydes, and morpholine

Journal of the American Chemical Society
Jinqiang Kuang, Shengming Ma

Abstract

ZnI(2) has been identified as the catalyst for the one-step synthesis of allenes from terminal alkynes and aldehydes with morpholine as the base in toluene. The reaction is believed to proceed via the intermediacy of propargylic amines, which was converted to allenes by a sequential hydride transfer and beta-elimination process. The reaction is applicable for both aromatic and aliphatic aldehydes. Functionalities such as halide, hydroxyl, or amine may be tolerated.

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Citations

Oct 29, 2010·Chemical Communications : Chem Comm·Pierrick NunSteven P Nolan
Mar 17, 2011·Chemical Communications : Chem Comm·Shichao Yu, Shengming Ma
Apr 13, 2011·Chemical Communications : Chem Comm·Venu SrinivasK C Kumara Swamy
Jan 31, 2012·Chemical Communications : Chem Comm·Shovan MondalMichèle P Bertrand
Dec 24, 2014·Organic & Biomolecular Chemistry·Clément F HeinrichLaurence Miesch
Aug 22, 2014·Organic & Biomolecular Chemistry·Qing-Han LiHan-Mou Gau
Jul 13, 2017·The Journal of Organic Chemistry·Maren Schaarschmidt, Klaus T Wanner
Aug 31, 2016·Topics in Current Chemistry·Liang Wang, Jian Xiao
Sep 18, 2013·Nature Communications·Xinjun TangShengming Ma
Mar 6, 2015·Organic & Biomolecular Chemistry·Jiasheng ZhangShengming Ma
May 29, 2018·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Mohammad Lokman Hossain, Jianbo Wang
Jan 25, 2012·Angewandte Chemie·Shichao Yu, Shengming Ma
Feb 27, 2013·Angewandte Chemie·Deepankar DasDaniel Seidel
Jan 24, 2019·Chemical Communications : Chem Comm·Jinqiang KuangDaesung Lee
Mar 15, 2012·Chemistry : a European Journal·María Paz MuñozMiguel Angel Sierra
Aug 22, 2013·Chemical Communications : Chem Comm·Xinjun TangShengming Ma
Sep 27, 2019·Organic & Biomolecular Chemistry·Kamran AmiriAhmed Al-Harrasi
Sep 13, 2013·Chemistry : a European Journal·Bo Peng, Nuno Maulide
Jun 26, 2012·Angewandte Chemie·Xuefeng GaoMichael Harmata
Dec 18, 2013·Angewandte Chemie·Shuai ShiA Stephen K Hashmi
Apr 8, 2014·Angewandte Chemie·Michael C Haibach, Daniel Seidel
Mar 8, 2019·Chemical Science·Yifan CuiShengming Ma
Mar 17, 2012·Chemical Society Reviews·Vsevolod A PeshkovErik V Van der Eycken
Nov 13, 2012·Chemistry : a European Journal·Juntao YeShengming Ma
Mar 6, 2012·Journal of Computational Chemistry·Marta GonzálezCarlos Silva López

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