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Regio- and Stereoselective Iodoacyloxylations of Alkynes

Author:
Priebbenow, Daniel L., Gable, Robert. W., Baell, Jonathan
Source:
Journal of organic chemistry 2015 v.80 no.9 pp. 4412-4418
ISSN:
1520-6904
Subject:
acids, alkynes, chemical reactions, chemical structure, esters, iodine, methodology, organic chemistry, regioselectivity, stereoselectivity
Abstract:
A new method for the regioselective and stereoselective iodoacyloxylation of alkynes has been developed. This protocol utilizes a combination of an iodobenzene dicarboxylate and iodine to functionalize a series of activated and unactivated alkynes in an entirely selective and predictable fashion. The resultant iodo-enol esters were subsequently coupled with boronic acids to afford tetrasubstituted alkene derivatives, which could be further converted to the corresponding 1,1-disubstituted acetophenone.
Agid:
5505362