We report the development of palladium(0)-catalyzed syn-selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B2 pin2 or PhMe2 Si-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 a directed 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.
We report the development of class="Chemical">palladium(0)-catalyzed class="Chemical">pan class="Gene">syn-selective 1,2-carboboration and -silylation reactions of alkenes containing cleavable directing groups. With B2 pin2 or PhMe2 Si-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 a directed 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.
Authors: Lucas J Oxtoby; Zi-Qi Li; Van T Tran; Tuğçe G Erbay; Ruohan Deng; Peng Liu; Keary M Engle Journal: Angew Chem Int Ed Engl Date: 2020-04-07 Impact factor: 15.336
Authors: Tao He; Zheng-Wang Qu; Hendrik F T Klare; Stefan Grimme; Martin Oestreich Journal: Angew Chem Int Ed Engl Date: 2022-04-19 Impact factor: 16.823
Authors: Nicolas Müller; Benedikt S Schreib; Sebastian U Leutenegger; Erick M Carreira Journal: Angew Chem Int Ed Engl Date: 2022-05-16 Impact factor: 16.823