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Cp*Rh(III)-catalyzed regioselective cyclization of aromatic amides with allenes.

Jing LiuDeng-Yin LiuQian YangYao-Fu ZengXiao-Li WangPeng-Fei WangYu-Jun RuanMiao-Miao WenShang-Shi ZhangLi-da DuXu-Ge Liu
Published in: Chemical communications (Cambridge, England) (2024)
A new Cp*Rh(III)-catalyzed regioselective cyclization reaction of aromatic amides with allenes is reported. The use of allenyl derivatives bearing a directing-group assistant as a reaction promoter was the key to the success of this protocol. In this catalytic system, N -(pivaloyloxy)benzamide substrates react with allenes via Rh-σ-alkenyl intermediates, while N -(pivaloyloxy) indol substrates react via Rh-π-allyl intermediates. These reactions were characterized by mild reaction conditions, a broad substrate scope, and high functional-group compatibility to yield several high-value isoquinolinone and pyrimido[1,6- a ]indol-1(2 H )-one skeleton-containing compounds. The synthetic applications and primary mechanisms were also investigated.
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