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.
The usual way to synthesize spiroindolinones is the application of isatin derivatives. Here, we report the first Pd‐catalyzed Buchwald–Hartwig addition–elimination strategy for the formation of the spiroindolinone–isoindolinone architecture. The application of the Ugi‐4‐component reaction (Ugi‐4CR) allows the facile introduction of diversity and increases the practicality of this protocol.
A cascade approach has been developed towards dual C-C bond formation via consecutive C-H functionalization/cyclization giving access to pyrrolo[1,2-a]indoles in a highly regio- and diastereoselective manner using catalytic [Ru(p-cymene)Cl]. The methodology was further expanded to attain pentacyclic structures involving manifold C-C bond creation.
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