Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives

Organic Letters
Peng-Hua LiMin Shi

Abstract

A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[ b]naphthalene derivatives in moderate to excellent yields under mild conditions.

References

Feb 15, 2001·Accounts of Chemical Research·T M Trnka, R H Grubbs
Sep 9, 2004·Chemical Society Reviews·Antonio M Echavarren, Cristina Nevado
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
Jul 19, 2008·Chemical Reviews·Eloísa Jiménez-Núñez, Antonio M Echavarren
Jul 25, 2009·Accounts of Chemical Research·Matthew T Whited, Robert H Grubbs
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Jun 4, 2010·Chemical Reviews·Min ShiHajime Maeda
Jul 8, 2010·Chemistry : a European Journal·Ahmad Masarwa, Ilan Marek
Apr 14, 2011·Organic Letters·Matthew HassinkJoseph M Fox
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
Sep 13, 2011·Organic Letters·Takuya OzawaSeijiro Matsubara
May 15, 2012·Accounts of Chemical Research·Huw M L Davies, Yajing Lian
Jul 17, 2012·Journal of the American Chemical Society·Erica BenedettiKay M Brummond
Jan 11, 2013·The Journal of Organic Chemistry·Mohammad Lokman HossainJianbo Wang
Mar 14, 2013·Chemical Communications : Chem Comm·Ping-Xin ZhouYong-Min Liang
Apr 4, 2013·Journal of the American Chemical Society·Todd K HysterTomislav Rovis
Aug 21, 2013·Chemical Society Reviews·Ana Caballero, Pedro J Pérez
Oct 31, 2013·Accounts of Chemical Research·Di-Han ZhangMin Shi
May 8, 2014·Chemical Society Reviews·Huw M L Davies, Joshua S Alford
Jan 24, 2015·Organic & Biomolecular Chemistry·Laura S KocsisEmmanuel A Theodorakis
Jun 19, 2015·Organic & Biomolecular Chemistry·Lei YuQing Xu
Jun 17, 2016·Angewandte Chemie·Minqiang Jia, Shengming Ma
Mar 30, 2017·Chemical Society Reviews·Ying Xia, Jianbo Wang
May 18, 2017·Chemical Communications : Chem Comm·Liu-Zhu YuMin Shi
Aug 24, 2017·Angewandte Chemie·Steven C SchmidJennifer M Schomaker
Sep 19, 2017·Journal of the American Chemical Society·Takeshi NanjoM Christina White

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