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Title: Directed, Nickel-Catalyzed 1,2-Alkylsulfenylation of Alkenyl Carbonyl Compounds
We report a regioselective, nickel-catalyzed syn-1,2-carbosulfenylation of non-conjugated alkenyl carbonyl compounds with alkyl/arylzinc nucleophiles and tailored N–S electrophiles. This method allows the simultaneous installation of a variety of C(sp3) and S(Ar) (or Se(Ar)) groups on to unactivated alkenes, which complements previously developed 1,2-carbosulfenylation methodology in which only C(sp2) nucleophiles are compatible. A bidentate directing auxiliary controls regioselectivity, promotes high syn-stereoselectivity with a variety of E- and Z- internal alkenes, and enables the use of a variety of electrophilic sulfenyl (and seleno) electrophiles. Among compatible electrophiles, those with N-alkyl-benzamide leaving groups were found to be especially effective, as determined through comprehensive structure–reactivity mapping.  more » « less
Award ID(s):
1800280
PAR ID:
10325940
Author(s) / Creator(s):
; ; ;
Date Published:
Journal Name:
Chemical Science
ISSN:
2041-6520
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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