Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand.

Org Lett

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Published: August 2021

AI Article Synopsis

  • The hydroformylation process allows for the synthesis of valuable (poly)enals from terminal arylalkynes and enynes, but has been challenging with terminal alkynes.
  • A new stable biphosphoramidite ligand with strong π-acceptor properties has been developed to improve the efficiency and selectivity of this reaction.
  • The Rh-catalyzed method yields important -(poly)enals in good amounts while maintaining excellent chemo- and regioselectivity under mild conditions.

Article Abstract

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important -(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c02140DOI Listing

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