Journal article

Regio- and Stereoselective Iodoacyloxylations of Alkynes

Daniel L Priebbenow, Robert W Gable, Jonathan Baell

JOURNAL OF ORGANIC CHEMISTRY | AMER CHEMICAL SOC | Published : 2015

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.

Grants

Awarded by Australian Research Council


Funding Acknowledgements

Funding from the Australian Research Council (DP140103996) is acknowledged. The authors also thank Assoc. Prof. Bernie Flynn for valuable discussions.