Rhodium-Catalyzed Regioselective C—O and C—C Bonds Formation of 3-Oxopent-4-enenitriles with Alkynes for the Synthesis of Polysubstituted 2H-Pyrans
Kelu Yan , Xiao Liu , Jiangwei Wen , Qiuyun Li , Junjie Wang , Yang Zheng , Xiu Wang
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (17) : 1986 -1992.
Rhodium-Catalyzed Regioselective C—O and C—C Bonds Formation of 3-Oxopent-4-enenitriles with Alkynes for the Synthesis of Polysubstituted 2H-Pyrans
The rhodium-catalyzed C—H bond activation and cyclization of 3-oxopent-4-enenitriles with alkynes proceed efficiently. Various 2 H-pyrans with multiple substituents are achieved in good yields through regioselective formation of C—O and C—C bonds. Transformations involving hydroxy-alkynoates resulted in products with a furo[3, 4- b]pyran skeleton via further intramolecular ester exchange processes. Different from the traditional “1-oxatrienes pathway”, this method for the synthesis of useful 2 H-pyrans possesses certain highlights in terms of readily available substrates, stable and easily derivatized products, gentle and convenient operation process, and step and atom economy.
Rhodium / C—H activation / 3-Oxopent-4-enenitriles / Alkynes / 2 H-Pyrans / Transition metals / Regioselectivity / Cyclization
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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