Catalytic Generation and Intermolecular Addition of Diarylmethyl Anions Utilizing [1,2]‐Phospha‐Brook Rearrangement Under Brønsted Base Catalysis

Abstract

AbstractAn 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 Brønsted 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 α,β‐unsaturated ketones, aryl aldehydes, α‐ketoesters, and N‐Boc imines, providing the corresponding diarylalkane derivatives in good yields.