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Here, we report a philicity-mismatched nickel-catalyzed C\u2013N cross-electrophile coupling (XEC) that combines electrophilic carbon and nitrogen precursors. Because the method relies on electrophilic nitrogen precursors, basic additives are not required to activate the nitrogen coupling partner. This mild protocol exhibits broad functional group tolerance, including base-sensitive substrates, and is compatible with late-stage applications. The electrophilic nitrogen precursors can be accessed from diverse starting materials, including C\u2013H bonds and olefins. We demonstrate a two-step, one-pot N-phenothiazination, C\u2013N XEC sequence that provides the platform for application of C\u2013N XEC to the functionalization of amine-containing bioactive small molecules. Strategic implementation of C\u2013N XEC enables synthesis of designer secondary and tertiary amines as well as unsymmetrical diamines. Mechanistic investigations indicate the C\u2013N XEC proceeds via a Ni(II)\u2013aryl-amido intermediate and enforces cross-selectivity by avoiding Ni(II)\u2013aryl-halide intermediates associated with homocoupling. These findings establish a paradigm for base-free C\u2013N bond construction and introduce a mechanistic rationale for controlling C\u2013X XEC selectivity.<\/jats:p>","DOI":"10.1021\/jacs.6c05089","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:05:01Z","timestamp":1785852301000},"page":"33104-33117","source":"Crossref","is-referenced-by-count":1,"title":["Base-Free\nC\u2013N Cross-Electrophile Coupling"],"prefix":"10.1021","volume":"148","author":[{"given":"Samya","family":"Samanta","sequence":"first","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lauv","family":"Patel","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diyasha","family":"Manna","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Melissa","family":"Ojeda","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3717-2001","authenticated-orcid":true,"given":"David C.","family":"Powers","sequence":"additional","affiliation":[{"name":"Texas A&M University , , , ,","place":["College Station, Texas, United States, 77843"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,31]]},"reference":[{"key":"2026081210100566700_cit1","doi-asserted-by":"publisher","first-page":"2651","DOI":"10.1021\/cr0505268","article-title":"Selected Patented Cross-Coupling Reaction Technologies","volume":"106","author":"Corbet","year":"2006","journal-title":"Chem. 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