Literature DB >> 17253830

Highly selective 5-substitution of 3-methylthiophene via directed lithiation.

Keith Smith1, Mark Lewis Barratt.   

Abstract

Lithiation of 3-methylthiophene with lithium 2,2,6,6-tetra-methylpiperidide (LiTMP) is highly selective at the 5-position, and reaction with a range of electrophiles gives high yields of the corresponding 2,4-disubstituted thiophenes, even when unhindered electrophiles are used.

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Year:  2007        PMID： 17253830     DOI： 10.1021/jo062024f

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


  4 in total

1.  Iridium-catalyzed borylation of thiophenes: versatile, synthetic elaboration founded on selective C-H functionalization.

Authors:  Ghayoor A Chotana; Venkata A Kallepalli; Robert E Maleczka; Milton R Smith
Journal:  Tetrahedron       Date:  2008-06-23       Impact factor: 2.457

2.  A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas.

Authors:  Keith Smith; Gamal A El-Hiti; Amany S Hegazy; Benson Kariuki
Journal:  Beilstein J Org Chem       Date:  2011-09-06       Impact factor: 2.883

3.  Influence of solvent mixture on nucleophilicity parameters: the case of pyrrolidine in methanol-acetonitrile.

Authors:  Salma Souissi; Wahiba Gabsi; Abderraouf Echaieb; Julien Roger; Jean-Cyrille Hierso; Paul Fleurat-Lessard; Taoufik Boubaker
Journal:  RSC Adv       Date:  2020-08-03       Impact factor: 4.036

4.  Potent new small-molecule inhibitor of botulinum neurotoxin serotype A endopeptidase developed by synthesis-based computer-aided molecular design.

Authors:  Yuan-Ping Pang; Anuradha Vummenthala; Rajesh K Mishra; Jewn Giew Park; Shaohua Wang; Jon Davis; Charles B Millard; James J Schmidt
Journal:  PLoS One       Date:  2009-11-10       Impact factor: 3.240
  4 in total

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