Literature DB >> 17629343

TiCl4-catalyzed indirect anti-Markovnikov hydration of alkynes: application to the synthesis of benzo[b]furans.

Lutz Ackermann1, Ludwig T Kaspar.   

Abstract

An efficient methodology for the indirect anti-Markovnikov hydration of unsymmetrically substituted terminal and internal alkynes is based on TiCl4-catalyzed hydroamination reactions. Its application to ortho-alkynylhaloarenes, followed by a copper-catalyzed O-arylation, provides flexible access to substituted benzo[b]furans.

Entities:  

Year:  2007        PMID： 17629343     DOI： 10.1021/jo070887i

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes.

Authors:  Yibiao Li; Liang Cheng; Xiaohang Liu; Bin Li; Ning Sun
Journal:  Beilstein J Org Chem       Date:  2014-12-04       Impact factor: 2.883

Review 2.  Synthesis of Oxygen Heterocycles via Aromatic C-O Bond Formation Using Arynes.

Authors:  Hideto Miyabe
Journal:  Molecules       Date:  2015-07-09       Impact factor: 4.411

3.  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

4.  Direct Arylation of Benzo[b]furan and Other Benzo-Fused Heterocycles.

Authors:  Toan Dao-Huy; Maximilian Haider; Fabian Glatz; Michael Schnürch; Marko D Mihovilovic
Journal:  European J Org Chem       Date:  2014-11-17

5.  Synthesis of Benzo[b]furans by Intramolecular C-O Bond Formation Using Iron and Copper Catalysis.

Authors:  Martyn C Henry; Andrew Sutherland
Journal:  Org Lett       Date:  2020-03-18       Impact factor: 6.005
  5 in total

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