A synthesis of 1,3-dienes using a Ni(II) mediated Suzuki-Miyaura reaction

Abstract

Synthesis of the 1,3-dienes from arylboronic acids with propargyl alcohols using a Ni(II) precatalysts is presented. Through detailed reaction screening NiCl₂(PCy₃)₂ has been identified as the optimal catalyst for this transformation. The reaction is thought to proceed through a Ni(II) allenyl complex, which undergoes a base free Suzuki-Miyaura cross-coupling through arylboronic acids, with the resultant aryl allene rearranging to its 1,3-diene. Application of these optimized reaction conditions then provides several dienes in reasonable to good, isolated yields.

KEY WORDS: Suzuki-Miyaura, NiCl₂(PCy₃)₂, 1,3-Dienes, Allenyl, Base free

Bull. Chem. Soc. Ethiop. 2024, 38(5), 1405-1412.                                                           

DOI: https://dx.doi.org/10.4314/bcse.v38i5.16