Metal-free, visible-light-promoted decarboxylative alkylation of Baylis–Hillman acetates with N-(acyloxy)phthalimides. Issue 18 (1st September 2022)

• Record Type: Journal Article
• Authors: Zhang, De-Run; Hu, Lin-Ping; Liu, Feng-Lin; Huang, Xiao-Hong; Li, Xia; Liu, Bo; Huang, Guo-Li
• Is Part Of: Green chemistry. Volume 24:Issue 18(2022)
• Page Start: 6840
• Page End: 6844
• Publication Date: 2022-09-01
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc02562k
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A visible light-driven metal- and oxidant-free procedure for the decarboxylative alkylation of Baylis–Hillman acetates with N -(acyloxy)phthalimides to access trisubstituted alkyl acrylates under mild reaction conditions is reported. Abstract : A visible-light-promoted decarboxylative alkylation of Baylis–Hillman acetates with N -(acyloxy)phthalimides to access trisubstituted alkyl acrylates under metal-free and mild reaction conditions was developed. A variety of N -(acyloxy)phthalimides derived from structurally diverse primary, secondary and tertiary aliphatic carboxylic acids could all smoothly convert to structurally diverse alkyl acrylates in this protocol. Interestingly, aliphatic carboxylic acids and acrylic esters derived from Baylis–Hillman acetates bearing a smaller steric structure show better stereoselectivity of the E configuration. This work offers an economic and easily handled approach to C(sp2)–C(sp2) and C(sp3)–C(sp3) bond formation in one step. Moreover, this protocol could be applied to the late-stage functionalization of natural products.