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Synfacts 2014; 10(1): 0031
DOI: 10.1055/s-0033-1340387
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Hypervalent Iodine for α,α-Dihalogenation

Contributor(s):
Timothy M. Swager
,
John B. Goods
Tao J, Tran R, Murphy GK * University of Waterloo, Canada
Dihaloiodoarenes: α,α-Dihalogenation of Phenylacetate Derivatives.

J. Am. Chem. Soc. 2013;
135: 16312-16315
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Further Information

Publication History

Publication Date:
13 December 2013 (online)

 
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Key words

α-halogenation - hypervalent iodine

Significance

Functionalization at the α-position of carbonyls represents one of the most versatile and useful types of transformations in organic chemistry. In this paper, the authors describe the use of a hypervalent iodine species to doubly ­halogenate the α-position of esters with either chlorine or fluorine.


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Comment

While the chlorination procedure was shown to be broadly functional group tolerant, the need for BF3·OEt2 in the case of fluorination limits the possible functionality in the starting material. The authors report that substrates with labile ­moieties such as OMe or NHAc decompose upon heating with BF3·OEt2.


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