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- Publisher
- Wiley
- Copyright
- © 2020 SIOC, CAS, Shanghai, & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 1001-604X
- eISSN
- 1614-7065
- DOI
- 10.1002/cjoc.202000044
- Publisher site
- See Article on Publisher Site
Abstract
It is known that Rh‐catalyzed reaction of propargylic alcohols with aryl metallic reagents undergoes SN2’‐type reaction affording allenes via a sequential arylmetalation and β‐OH elimination process. Here we report a Rh/Ag‐cocatalyzed reaction of propargylic alcohols with organoboronic acids affording stereo‐defined (E)‐3‐arylallylic alcohols via arylmetalation and protodemetalation with a high regio‐ and stereoselectivity under very mild conditions. The reaction exhibits a good substrate scope and the compatibility with synthetically useful functional groups with no racemization for optically active propargylic alcohols. Such a reaction may also be extended to homopropargylic alcohols with a remarkable regioselectivity and exclusive E‐stereoselectivity.
Journal
Chinese Journal of Chemistry – Wiley
Published: Apr 1, 2020
Keywords: ; ; ; ;