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Sustainable Carbonyl Acetalization Enabled by Frustrated Ion-Pair under Mild Conditions
Ruoqi Li1, Lina Huang1, Peng Chen1
1Henan Linker Technology Key Laboratory, College of Advanced Interdisciplinary Science and Technology (CAIST), Henan University of Technology, Zhengzhou 450001, China.
None:
Acetalization represents a fundamental transformation for the protection of carbonyls and functional-group interconversion in organic synthesis. Herein, we report a metal-free dehydrative acetalization of aldehydes and ketones, including isatins with alcohols enabled by a frustrated triarylcarbenium ion pair as the catalyst. The reactions proceeded under mild conditions, and a broad range of acetal products was obtained up to 98% yield with excellent functional-group tolerance, including the late-stage protection of complex pharmaceutical molecules. Moreover, this protocol demonstrated high efficiency at lower catalyst loading, and the acetalization was readily scalable through continuous-flow processing to the gram level. Mechanistic studies supported a probable SN1-type pathway mediated by this frustrated ion pair.
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