Nickel-Catalyzed C(sp³)–Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products

Abstract

In this study, we present a nickel-catalyzed reductive C(sp 3 )−Sb coupling of unactivated alkyl chlorides with chlorostibines. This approach is highly versatile, tolerating various functional groups such as acetal, alkene, nitrile, amine, ester, silyl ether, thioether, and various heterocyclic compounds. Notably, the late-stage modification of bioactive molecules and the satisfactory anticancer activity against cancerous MDA-MB-231 also demonstrate the potential application.

Nickel-catalyzed γ-alkylation of cyclopropyl ketones with unactivated primary alkyl chlorides: balancing reactivity and selectivity via halide exchange

“…of Ni(COD) 2 , the corresponding product 3aa could be yielded in 26%, indicating the coupling started with Ni(0) species ( Scheme 3E ). 16 Finally, phenethylzinc chloride 5 (0.25 M) 17 was synthesized and subjected to the reaction with 1a in the absence of zinc powder ( Scheme 3F ). These experimental results support that excludes the possibility of an organozinc reagent in the reaction system.…”

Catalyst-Free, Zn-Mediated Decarboxylative Coupling of Chlorostibines to Access Alkylstibines with Stable C(sp3)–Sb Bonds

“…These applications include their use in living radical polymerization, as alkylation reagents, as starting materials for metal–organic chemical vapor deposition, to enhance the magnetic properties of 3d metal centers through ligand effects, and to improve the catalytic properties of metal complexes through co-ligand effects, and the alkylstibines exhibit antitumor activity . Previously, we developed a nickel-catalyzed cross-coupling reaction for C(sp 3 )–Sb bonds from chlorostibines with alkyl boronic acids and alkyl halides, but the benzylation of organostibines, as well as the construction of C(sp 3 )–Sb bonds from natural products, drug molecules, and some complex alkyl blocks, remains challenging. Therefore, a general and efficient procedure for the synthesis of alkylstibines is still in great demand.…”