Regioselective 1,2-carbosulfenylation of unactivated alkenes via directed nickel catalysis

• Main Authors: Li, W. (Author), Meng, X. (Author), Shen, Q. (Author), Wang, C. (Author), Xie, L. (Author), Zhang, L. (Author), Zhu, L. (Author)
• Format: Article
• Language: English
• Published: Royal Society of Chemistry 2022
• Subjects: Alkene substrate; Amines; Aryl group; Catalysis; Chemo-and regioselectivities; Chiral centers; Directing groups; Electrophiles; Enantioselectivity; Homoallylic amines; Nickel; Nickel catalysis; Olefins; Regio-selective; Regioselectivity; Sulfur compounds; Three-component
• Online Access: View Fulltext in Publisher

 A bidentate directing group-assisted Ni-catalyzed three component 1,2-carbosulfenylation of unactivated alkenes with aryl/alkenylboronic acids and disulfide electrophiles is reported. The reaction affords the desired products with high levels of chemo- and regioselectivity. A wide range of aryl groups and sulfur moieties can be simultaneously installed in both internal and terminal homoallylic amines with excellent functional group tolerance. Notably, the alkene substrates with a chiral center at the α-position furnish α,γ-dibranched thiolamines with high diastereoselectivity and enantioselectivity that would otherwise be difficult to synthesize. The generality and scalability could make this method attractive for preparing complex organosulfur compounds. © 2022 The Royal Society of Chemistry.