Literature DB >> 20302324

Expeditious synthesis of benzopyrans via Lewis acid-catalyzed C-H functionalization: remarkable enhancement of reactivity by an ortho substituent.

Keiji Mori1, Taro Kawasaki, Shosaku Sueoka, Takahiko Akiyama.   

Abstract

An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.

Entities:  

Year:  2010        PMID: 20302324     DOI: 10.1021/ol100316k

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


  3 in total

1.  C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors:  Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal:  J Org Chem       Date:  2012-06-06       Impact factor: 4.354

2.  2-(2-{2-[2-(Dibromo-meth-yl)phen-oxy]eth-oxy}benz-yloxy)benzaldehyde.

Authors:  Juan Xia; Xiang Liu; An-Qi Wang; Zhong-Xing Su
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-26

3.  Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)-H bond functionalization.

Authors:  Keiji Mori; Nobuaki Umehara; Takahiko Akiyama
Journal:  Chem Sci       Date:  2018-06-25       Impact factor: 9.825

  3 in total

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