Divergent Conversion of Double Isocyanides with Alkenyl Bromide to Polysubstituted Pyrroles and 4‑Imino-4,5-dihydropyrrolo[3,4‑b]pyrrol-6(1H)‑one Derivatives by Pd-Catalyzed Tandem Cyclization Reactions

Herein a novel and concise approach to pyrrole skeletons via Pd-catalyzed tandem cyclization reactions is investigated. The substrates for the transformation could be readily prepared by phosphoric acid-catalyzed Ugi reactions with available starting materials. In this strategy, two isocyanides part...

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Published inOrganic letters Vol. 24; no. 3; pp. 859 - 863
Main Authors Ren, Zhi-Lin, Qiu, Ji-Ying, Yuan, Ling-Ling, Yuan, Yue-Fei, Cai, Shuang, Li, Jun, Kong, Chi, He, Ping, Wang, Long
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 28.01.2022
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Summary:Herein a novel and concise approach to pyrrole skeletons via Pd-catalyzed tandem cyclization reactions is investigated. The substrates for the transformation could be readily prepared by phosphoric acid-catalyzed Ugi reactions with available starting materials. In this strategy, two isocyanides participate in sequential isocyanide insertion reactions, and the chemoselectivity of the products is regulated by the steric hindrance of the isocyanide. A plausible mechanism for the formation of the corresponding adducts is proposed.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c04146