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Catalytic Generation and Intermolecular Addition of Diarylmethyl Anions Utilizing [1,2]-Phospha-Brook Rearrangement Under Br?nsted Base Catalysis

ADVANCED SYNTHESIS & CATALYSIS(2024)

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Abstract
An intermolecular addition reaction involving an unconventional combination of a diarylmethyl anion and an electrophile, which is mediated by the [1,2]-phospha-Brook rearrangement under Bronsted base catalysis, was developed. Diarylmethyl anions having a benzofuran moiety were generated through the rearrangement with the aid of a catalytic amount of phosphazene base P2-tBu. The resulting carbanion intermediates were trapped by various electrophiles, such as alpha,beta-unsaturated ketones, aryl aldehydes, alpha-ketoesters, and N-Boc imines, providing the corresponding diarylalkane derivatives in good yields. image
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Key words
Bronsted base catalysis,Carbanions,Phospha-Brook rearrangement,Diarylalkanes,Phosphazenes
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