Regioselective Cp*Ir(III)-Catalyzed Allylic C–H Sulfamidation of Allylbenzene Derivatives

Kazerouni, Amaan M.; Nelson, Taylor A. F.; Chen, Steven W.; Sharp, Kimberly R.; Blakey, Simon B.

Regioselective Cp*Ir(III)-Catalyzed Allylic C–H Sulfamidation of Allylbenzene Derivatives

2019

Kazerouni, Amaan M. | Nelson, Taylor A. F. | Chen, Steven W. | Sharp, Kimberly R. | Blakey, Simon B.

In this study we report the development of the regioselective Cp*Ir(III)-catalyzed allylic C–H sulfamidation of allylbenzene derivatives, using azides as the nitrogen source. The reaction putatively proceeds through a Cp*Ir(III)-π-allyl intermediate and demonstrates exclusive regioselectivity for the branched position of the π-allyl. The reaction performs well on electron-rich and electron-deficient allylbenzene derivatives and is tolerant of a wide range of functional groups, including carbamates, esters, and ketones. The proposed mechanism for this reaction proceeds via C–N reductive elimination from a Cp*Ir(V) nitrenoid complex at the branched position of the π-allyl.

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