Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the sigma-alkylpalladium intermediate with boron

Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the sigma-alkylpalladium intermediate with boron

Pd-catalyzed domino Heck/borylation of acrylamides with B2pin2 is reported to generate synthetically useful indolinone-3-methyl boronic esters, via capturing σ-alkyl palladium with boron. Further functionalization of the obtained boronic ester qualify it as a new starting point for the functionaliza...

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Veröffentlicht in:Chemical Communications 2015, Vol.51 (80), p.14862-14865
Hauptverfasser: Vachhani, Dipak D, Butani, Himanshu H, Sharma, Nandini, Bhoya, Umed C, Van der Eycken, Erik, Shahb, Anamik K
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container_end_page 14865
container_issue 80
container_start_page 14862
container_title Chemical Communications
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creator Vachhani, Dipak D
Butani, Himanshu H
Sharma, Nandini
Bhoya, Umed C
Van der Eycken, Erik
Shahb, Anamik K
description Pd-catalyzed domino Heck/borylation of acrylamides with B2pin2 is reported to generate synthetically useful indolinone-3-methyl boronic esters, via capturing σ-alkyl palladium with boron. Further functionalization of the obtained boronic ester qualify it as a new starting point for the functionalization of specific C(sp(3))-H bond. Moreover, the application of an Ugi-adduct as starting material or B2nep2 as an alternative boron source works equally well, making this a broadly applicable and robust method for the formation of a C-C and C-B bond in a single operation.
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title Domino Heck/borylation sequence towards indolinone-3-methyl boronic esters: trapping of the sigma-alkylpalladium intermediate with boron
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