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DOI: 10.1055/sos-SD-109-00525

Tobrman, T.Science of Synthesis Knowledge Updates, (20241151.

Transient 2H-phospholes have been applied only rarely for the preparation of substituted 1H-phospholes. A recent preparation of unsymmetrically substituted 1H-phospholes is based on the reaction of 1-aryl-3,4-dimethyl-1H-phospholes (e.g., 66), which isomerize to 2H-phospholes (e.g., 67). Subsequently, the transient 2H-phosphole is deprotonated to give a phospholide ion (e.g., 68). Then, copper-catalyzed PC bond formation and repetition of the above reaction sequence completes the synthesis of the pentasubstituted phosphole (e.g., 69) (Scheme 28). The developed process allows smooth introduction of aryl and alkenyl substituents.[‌93‌]

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