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Efficient catalytic turnover is facilitated using a tailored N\u2212S electrophile containing an\n                    <jats:italic>N<\/jats:italic>\n                    \u2010methyl methanesulfonamide leaving group, allowing catalyst loadings as low as 1\u2005mol\u2009%. Regioselectivity is controlled by a collection of monodentate, weakly coordinating native directing groups, including sulfonamides, amides, sulfinamides, phosphoramides, and carbamates. Key to the development of this transformation is the identification of quinones as a family of hemilabile and redox\u2010active ligands that tune the steric and electronic properties of the metal throughout the catalytic cycle. Density functional theory (DFT) results show that the duroquinone (DQ) ligand adopts different coordination modes in different stages of the Ni\u2010catalyzed 1,2\u2010carbosulfenylation\u2010binding as an \u03b7\n                    <jats:sup>6<\/jats:sup>\n                    capping ligand to stabilize the precatalyst\/resting state and prevent catalyst decomposition, binding as an X\u2010type redox\u2010active durosemiquinone radical anion to promote alkene migratory insertion with a less distorted square planar Ni(II) center, and binding as an L\u2010type ligand to promote N\u2212S oxidative addition at a relatively more electron\u2010rich Ni(I) center.\n                  <\/jats:p>","DOI":"10.1002\/anie.202411870","type":"journal-article","created":{"date-parts":[[2024,9,2]],"date-time":"2024-09-02T11:24:07Z","timestamp":1725276247000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Hemilabile and Redox\u2010Active Quinone Ligands Unlock sp\n                    <sup>3<\/sup>\n                    \u2010Rich Couplings in Nickel\u2010Catalyzed Olefin Carbosulfenylation"],"prefix":"10.1002","volume":"63","author":[{"given":"Zi\u2010Qi","family":"Li","sequence":"first","affiliation":[{"name":"Department of Chemistry The Scripps Research Institute  10550\u2005N. 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