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- W4306174517 abstract "Herein, the first use of perfluoroalcohol H-bonding in accelerating acyclic azadiene inverse electron demand cycloaddition reactions is described, and its use in the promotion of heterocyclic azadiene cycloaddition reactions is generalized through examination of a complete range of azadienes. The scope of dienophiles was comprehensively explored; relative reactivity trends and solvent compatibilities were established with respect to the dienophile as well as azadiene; H-bonding solvent effects that lead to rate enhancements, yield improvements, and their impact on regioselectivity and mode of cycloaddition are defined; new viable diene/dienophile reaction partners in the cycloaddition reactions are disclosed; and key comparison rate constants are reported. The perfluoroalcohol effectiveness at accelerating an inverse electron demand Diels–Alder cycloaddition is directly correlated with its H-bond potential (pKa). Not only are the reactions of electron-rich dienophiles accelerated but those of strained and even unactivated alkenes and alkynes are improved, including representative bioorthogonal click reactions." @default.
- W4306174517 created "2022-10-14" @default.
- W4306174517 creator A5046866947 @default.
- W4306174517 creator A5049235255 @default.
- W4306174517 date "2022-10-14" @default.
- W4306174517 modified "2023-09-23" @default.
- W4306174517 title "Acyclic and Heterocyclic Azadiene Diels–Alder Reactions Promoted by Perfluoroalcohol Solvent Hydrogen Bonding: Comprehensive Examination of Scope" @default.
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- W4306174517 doi "https://doi.org/10.1021/acs.joc.2c02000" @default.
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