Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 11, Pages 5688-5692Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202015249
Keywords
1,4-enynes; alkynylation; allylic C-H activation; allyl-iridium complex; regioselectivity
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Funding
- Deutsche Forschungsgemeinschaft (Leibniz Award)
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This study presents a highly regioselective and redox-neutral protocol for constructing 1,4-enynes from unactivated olefins and bromoalkynes through intermolecular allylic C-H alkynylation. The developed mild reaction conditions are tolerant of a broad range of common functional groups, allowing for selective alkynylation of allylic C-H bonds in the presence of other directing groups. Mechanistic experiments support an intermolecular allylic C-H activation followed by electrophilic alkynylation.
Herein, we report a Cp*Ir-III-catalyzed highly regioselective and redox-neutral protocol for the construction of 1,4-enynes from unactivated olefins and bromoalkynes via intermolecular allylic C-H alkynylation. The developed mild reaction conditions tolerate a broad range of common functional groups, even enabling selective alkynylation of allylic C-H bonds in the presence of other prominent directing groups. Mechanistic experiments including the isolation of a catalytically active Ir-III-allyl species support an intermolecular allylic C-H activation followed by an electrophilic alkynylation.
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