Work

Highly selective palladium-catalyzed one-pot, five-fold B–H/C–H cross coupling of monocarboranes with alkenes

Year: 2019

Type: article

Abstract: Palladium-catalyzed dehydrogenative B-H/C-H cross coupling of monocarborane anions with alkenes is reported, allowing for the first time the isolation of selectively penta-alkenylated boron clusters. The reaction cascade is regioselective for the cage positions, leading directly to B2-6 functionalization. Under mild and convenient conditions, styrenes, benzylic alkenes and aliphatic alkenes are demonstrated to be viable coupling partners with exclusive vinyl-type B-C bond formation. Multiple subsequent transformations provide access to directing group-free products, chiral derivatives and penta-alkylated cages. The five-fold coupling, combined with the latter reactions, represents a powerful methodology for the straightforward synthesis of new classes of boron clusters.

Source: Chemical Science

DOI: 10.1039/c9sc00078j

Authors: Yunjun Shen, Kang Zhang, Xuewei Liang, Rakesh Dontha, Simon Duttwyler

Institution: Zhejiang University

Language: English

Topic: Boron Compounds in Chemistry

Subfield: Radiology, Nuclear Medicine and Imaging

Field: Medicine

Domain: Health Sciences

Open Access status: diamond

Funders: National Natural Science Foundation of China, Zhejiang University, Universität Zürich, National Key Research and Development Program of China

Awards: G2101271366, G2717198908, G3982039669, G8008360860