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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Rh(III)-Catalyzed [4 + 2] Self-Annulation of N-Vinylarylamides
Rui Sun1, Xiao Yang1, Xue Chen1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry , Sichuan University Chengdu 610064 , P. R. China.
Abstract:
An efficient rhodium(III)-catalyzed self-annulation of N-vinylarylamide has been developed. This reaction features a simple system and good reactivity with complete regioselectivity. The protocol provides easy access to an aminal incorporated dihydroisoquinolinone, which proved to be a versatile synthetic synthon. The kinetic isotope effect experiments showed that C-H activation is the rate-limiting step, and competition studies revealed the annulation exhibits a strong self-recognition mode. In addition, a seven-membered rhodacycle species was isolated and established as the key reaction intermediate.
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