Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 20, Pages 13179-13185Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01816
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Funding
- National Science Foundation (NSF) under the CCI Center for Selective C-H Functionalization [CHE-1700982]
- NSF [CHE-1531620]
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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)-pi-allyl intermediate and demonstrates exclusive regioselectivity for the branched position of the pi-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 pi-allyl.
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