Literature DB >> 16774261

2,3-disubstituted benzofuran and indole by copper-mediated C-C bond extension reaction of 3-zinciobenzoheterole.

Masaharu Nakamura1, Laurean Ilies, Saika Otsubo, Eiichi Nakamura.   

Abstract

[reaction: see text] A metalative 5-endo-dig cyclization reaction of 2-ynylphenoles or anilines effected by BuLi and ZnCl(2) produces 3-zinciobenzoheteroles in excellent yield. These intermediates have been transmetalated to the corresponding cuprates and allowed to react with electrophiles to produce a variety of 2,3-disubstituted benzofurans and indoles.

Entities:  

Year:  2006        PMID： 16774261     DOI： 10.1021/ol060896y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  A cycloisomerization/Friedel-Crafts alkylation strategy for the synthesis of pyrano[3,4-b]indoles.

Authors:  Matthew R Medeiros; Scott E Schaus; John A Porco
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

2.  Facile synthesis of 2-substituted benzo[b]furans and indoles by copper-catalyzed intramolecular cyclization of 2-alkynyl phenols and tosylanilines.

Authors:  Zhouting Rong; Kexin Gao; Lei Zhou; Jianyuan Lin; Guoying Qian
Journal:  RSC Adv       Date:  2019-06-07       Impact factor: 4.036

3.  Transition-metal-free base catalyzed intramolecular cyclization of 2-ynylphenols for efficient and facile synthesis of 2-substituted benzo[b]furans.

Authors:  Yong Liu; Tao Lu; Wei-Fang Tang; Jian Gao
Journal:  RSC Adv       Date:  2018-08-10       Impact factor: 3.361
  3 in total

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