Carbonylative Suzuki–Miyaura and Sonogashira Coupling Reactions with CO₂ as a C1 Source

Key words

carbonylation - Suzuki–Miyaura coupling - Sonogashira coupling - carbon dioxide - photocatalysis - metal–organic framework

Significance

A porphyrin-based metal–organic framework containing cobalt, copper, and palladium [(Cu₁Pd₂)_1.3@PCN-222(Co)], prepared according to Equation 1, catalyzed the carbonylative Suzuki–Miyaura coupling of aryl iodides with arylboronic acids and CO₂ as a C1 source in the presence of Et₃N and K₂CO₃ under visible-light irradiation to give the corresponding benzophenone derivatives in up to 90% yield. Similarly, arylboronic acids and aralkynes underwent carbonylative Sonogashira coupling reactions to give the corresponding diaryl alkynes in up to 87% yield.

Comment

The cobalt sites of (Cu₁Pd₂)_1.3@PCN-222(Co) catalyze the photoreduction of CO₂ under visible-light irradiation to give CO, which serves as a C1 source. Under an argon atmosphere, the Suzuki–Miyaura coupling reaction of iodobenzene and phenylboronic acid gave biphenyl. In the reaction of iodobenzene with phenylboronic acid and CO₂, the catalyst was recovered and reused four times without significant loss of its catalytic activity.

Publication History

Article published online:
16 February 2022