Issue 10, 2014

Applications of pentafluorophenyl boron reagents in the synthesis of heterocyclic and aromatic compounds

Abstract

Recently, main group reagents have attracted a lot of attention in bond-forming reactions in organic synthesis. This article highlights the use of pentafluorophenyl substituted boron reagents in their reactions with C[double bond, length as m-dash]C and C[triple bond, length as m-dash]C π-bonds for the synthesis of heterocyclic and aromatic compounds. These cyclisation reactions fall into four general classes although there is some overlap between classes and often combinations of these different types of reactivity are observed in the formation of the final heterocyclic product: (i) 1,2- (and 1,4-) additions of nucleophile and Lewis-acidic boron centre, (ii) 1,1-carboboration, (iii) carbocation rearrangements and (iv) cycloaddition chemistry. In addition, the prospect of using such boron reagents catalytically in the synthesis of aromatic compounds such as oxazoles and dibenzopentalene derivatives is emphasised.

Graphical abstract: Applications of pentafluorophenyl boron reagents in the synthesis of heterocyclic and aromatic compounds

Article information

Article type
Feature Article
Submitted
18 Oct 2013
Accepted
21 Nov 2013
First published
22 Nov 2013

Chem. Commun., 2014,50, 1161-1174

Applications of pentafluorophenyl boron reagents in the synthesis of heterocyclic and aromatic compounds

R. L. Melen, Chem. Commun., 2014, 50, 1161 DOI: 10.1039/C3CC48036D

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