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It has been proposed that \u201crate matching\u201d between the oxidative addition of the aryl halide and the rate of formation of the alkyl radical, in addition to the stability of the Ni(II)\u2013Ar complex, dictates the yield of the cross-coupling product. To probe this quantitatively, we developed a new tridentate monoanionic ligand that activatesalkyl and aryl chlorides and exhibits well-behaved electrochemistry, allowing the measurement of relative rate constants. This provides a framework to interrogate the rate-matching concept using both aryl and alkyl bromides and chlorides in cross-electrophile coupling. By combining an electroanalytical workflow with machine learning, the prediction of activation rate constants for all aryl\/alkyl chlorides and bromides was achieved and correlated with reaction yields. We found that productive coupling occurs in a specific rate regime, and the synthetic performance could be predictably modulated by choosing the \u201cmatched\u201d halide (either chloride or bromide) for each coupling partner.<\/jats:p>","DOI":"10.1021\/jacs.6c10810","type":"journal-article","created":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T16:16:52Z","timestamp":1790007412000},"page":"42104-42120","source":"Crossref","is-referenced-by-count":0,"title":["Using Data Science\nTools to Explore Rate Matching\nin a Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl and Aryl\nHalides (Cl, Br) with a Tridentate Monoanionic Ligand"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-0454-4940","authenticated-orcid":true,"given":"Haruka","family":"Takenaka","sequence":"first","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra J.","family":"Ring","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1102-8581","authenticated-orcid":true,"given":"Avijit","family":"Hazra","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Therese H.","family":"Wild","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samuel M. R.","family":"Powell","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tianhua","family":"Tang","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8244-9300","authenticated-orcid":true,"given":"Sarah E.","family":"Reisman","sequence":"additional","affiliation":[{"name":"California Institute of Technology , , , ,","place":["Pasadena, California, United States, 91125"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5746-8830","authenticated-orcid":true,"given":"Matthew S.","family":"Sigman","sequence":"additional","affiliation":[{"name":"University of Utah , , 315 South 1400 East , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"issue":"23","key":"2026100711115244000_cit1","doi-asserted-by":"publisher","first-page":"13397","DOI":"10.1021\/acs.chemrev.4c00524","article-title":"Cross-Electrophile\nCoupling: Principles, Methods, and Applications in Synthesis","volume":"124","author":"Ehehalt","year":"2024","journal-title":"Chem. 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Chem."},{"issue":"43","key":"2026100711115244000_cit5","doi-asserted-by":"publisher","first-page":"16192","DOI":"10.1021\/ja407589e","article-title":"Mechanism and Selectivity\nin Nickel-Catalyzed Cross-Electrophile\nCoupling of Aryl Halides with Alkyl Halides","volume":"135","author":"Biswas","year":"2013","journal-title":"J. Am. Chem. Soc."},{"issue":"4","key":"2026100711115244000_cit6","doi-asserted-by":"publisher","first-page":"39","DOI":"10.20517\/cs.2023.20","article-title":"Mechanisms of Nickel-Catalyzed Reductive\nCross-Coupling Reactions","volume":"3","author":"Wu","year":"2023","journal-title":"Chem. Synth."},{"key":"2026100711115244000_cit7","doi-asserted-by":"publisher","first-page":"130","DOI":"10.1016\/j.jorganchem.2014.08.015","article-title":"DFT Study of the Single Electron\nTransfer Mechanisms in Ni-Catalyzed Reductive Cross-Coupling of Aryl\nBromide and Alkyl Bromide","volume":"770","author":"Ren","year":"2014","journal-title":"J. Organomet. 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