Atom transfer cyclization catalyzed by InCl3 via halogen activation

Organic Letters
Gregory R Cook, Ryuji Hayashi

Abstract

[reaction: see text] Indium trichloride was found to be an efficient catalyst for the cyclization of allylic halides and alkynes with atom transfer in methylene chloride. Mechanistic evidence supports a cationic reaction pathway with Lewis acid activation of the allylic halogen. Concomitant nucleophilic attack by the alkyne and trapping with halide led to atom transfer cyclization products. Depending on alkyne substitution, a bromine atom was transferred from the substrate or a chlorine atom was transferred from the solvent.

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Citations

Oct 5, 2016·Accounts of Chemical Research·Dinesh KumarGregory R Cook
Aug 11, 2006·Organic Letters·Rubén M CarballoJuan I Padrón
Jan 6, 2009·Tetrahedron Letters·Ryuji Hayashi, Gregory R Cook
Mar 7, 2007·Angewandte Chemie·Susana Porcel, Antonio M Echavarren
Aug 7, 2010·Chemistry : a European Journal·Tatsuya WadaKoichiro Oshima
Jan 12, 2010·Chemical Communications : Chem Comm·Takami MorishitaJoji Ohshita
Nov 10, 2013·Chemistry, an Asian Journal·Masayuki IwasakiYasushi Nishihara
Aug 20, 2016·Angewandte Chemie·Stalin R PathipatiNicklas Selander
Apr 10, 2008·Organic Letters·Kosuke NambaMugio Nishizawa
Oct 7, 2008·The Journal of Organic Chemistry·Jhih-Meng TangRai-Shung Liu
Aug 26, 2009·The Journal of Organic Chemistry·Debasis SamantaGregory R Cook
Jan 18, 2018·ACS Omega·Ngangbam Renubala DeviAnil K Saikia

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