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

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 grou...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (11), p.3068-3074
Main Authors: Zhu, Lin, Meng, Xiao, Xie, Leipeng, Shen, Qiuyang, Li, Wenyi, Zhang, Lanlan, Wang, Chao
Format: Article
Language:English
Subjects:
Alkenes
Amines
Aromatic compounds
Catalysis
Enantiomers
Functional groups
Nickel
Organic chemistry
Organosulfur compounds
Regioselectivity
Stereoselectivity
Substrates
Sulfur
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Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00396a