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Pd(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol via a Chiral Auxiliary

preprint
revised on 22.07.2019 and posted on 22.07.2019 by Zhen Liu, Jiahao Chen, Xiaohan Li, Yang Gao, John Coombs, Matthew Goldfogel, Keary Engle
We report the development of palladium(0)-catalyzed syn-selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B2pin2or PhMe2Si–Bpin as nucleophiles and aryl/alkenyl triflates as electrophiles, a broad range of mono-, di-, tri- and tetrasubstituted alkenes are compatible in these transformations. We further describe directed a dearomative 1,2-carboboration of electron-rich heteroarenes by employing this approach. Through use of a removable chiral directing group, we demonstrate the viability of achieving stereoinduction in Heck-type alkene 1,2-difunctionalization. This work introduces new avenues to access highly functionalized boronates and silanes with precise regio- and stereocontrol.

Funding

NIH-5R35GM125052-02

Bristol-Myers Squibb Unrestricted Grant

Bristol-Myers Squibb Graduate Fellowship

Nankai University College of Chemistry International Research Scholarship

Alfred P. Sloan Fellowship

Camille-Dreyfus Teacher Scholar Award

History

Email Address of Submitting Author

keary@scripps.edu

Institution

The Scripps Research Institute

Country

USA

ORCID For Submitting Author

0000-0003-2767-6556

Declaration of Conflict of Interest

No conflict of interest to declare.

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