AI Article Synopsis
- A new nickel-catalyzed process enables selective addition of sulfur (or selenium) and carbon groups to non-conjugated alkenyl carbonyl compounds using different types of zinc nucleophiles and customized N-S electrophiles.
- This method expands upon existing techniques by allowing both carbon and sulfur-based nucleophiles to react with unactivated alkenes, enhancing previous 1,2-carbosulfenylation approaches that were limited to carbon nucleophiles.
- A specific bidentate directing auxiliary improves regioselectivity and stereoselectivity, working well with various alkenes and a range of effective electrophiles that include those with certain alkyl-benzamide leaving groups.
Article Abstract
We report a regioselective, nickel-catalyzed -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(sp) and S(Ar) (or Se(Ar)) groups onto unactivated alkenes, which complements previously developed 1,2-carbosulfenylation methodology in which only C(sp) nucleophiles are compatible. A bidentate directing auxiliary controls regioselectivity, promotes high -stereoselectivity with a variety of - and -internal alkenes, and enables the use of an array of electrophilic sulfenyl (and seleno) electrophiles. Among compatible electrophiles, those with -alkyl-benzamide leaving groups were found to be especially effective, as determined through comprehensive structure-reactivity mapping.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9172569 | PMC |
| http://dx.doi.org/10.1039/d2sc01563c | DOI Listing |
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