Promotion Mechanism of H₂O for Stereoselectivity in Pd(II)-catalyzed C―H Arylation of Diarylphosphinamides with Arylboronic Acids

Abstract

On the basis of a series of control experiments and nuclear magnetic resonance analyses, it is discovered that Boc-protected amino acid ligand coordinated to Pd center is partly replaced by N,N-dimethylformamide, and H₂O can inhibit coordination of N,N-dimethylformamide to Pd center. The novel action mechanism perfectly explains H₂O promotion for stereoselectivity in Pd(II)-catalyzed C―H arylation of diarylphosphinamides with arylboronic acids.

Keywords

C―H activation / Stereoselectivity / Water / Ligand exchange

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