Highly Regioselective and E/ Z-Selective Hydroalkylation of Ynone, Ynoate, and Ynamide via Photoredox Mediated Ni/Ir Dual Catalysis.

Org Lett

Department of Chemistry, College of Natural Sciences , Seoul National University, 1 Gwanak-ro, Gwanak-gu , Seoul 08826 , Republic of Korea.

Published: August 2018

AI Article Synopsis

  • Achieved selective hydroalkylation of ynone, ynoate, and ynamide using dual catalysis with Ni and Ir under light, yielding valuable trisubstituted enones.
  • The reaction was highly efficient, focusing on forming α/Z isomers, which adds to existing β-alkylation methods.
  • The resulting trisubstituted enones can be further modified into more useful compounds through subsequent reactions.

Article Abstract

Exclusively α- and highly E/ Z-selective hydroalkylation of ynone, ynoate, and ynamide was achieved via photoredox mediated Ni/Ir dual catalysis with high atom and step economy, producing trisubstituted enones, which are versatile synthetic building blocks. The developed reaction selectively delivered the α/ Z isomer, which is complementary to the previously reported β-alkylation processes. The trisubstituted enones could be transformed to more valuable compounds via post-functionalization.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b02017DOI Listing

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