Transition metal-catalyzed cross-coupling reactions have created an epoch in modern synthetic organic chemistry, offering a variety of insights into retrosynthetic tactics for synthesizing targeted complex molecules in medicine and materials-based applications. Despite numerous types of combinations of nucleophiles, electrophiles, and transition metal catalysts available for the cross-coupling reactions, construction of covalent bonds that include sp(3)-hybridized carbon(s) remains a challenge because of the inherent diverse reactivity of the alkyl species (i.e., alkyl halides and alkyl metals) involved in the catalytic cycle. Methods for leveraging alkyl radicals have recently emerged, which will aid in the realization of this goal. This perspective highlights and discusses recent advances in transition metal-catalyzed cross coupling reactions that engage alkyl radicals for C(sp(3))-N and C(sp(3))-Si bond formation with alkyl halides as well as use of carboxylic acid derivatives as surrogates of alkyl halides in decarboxylative C(sp(3))-C(sp(2))/C(sp(3))/B couplings.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Qin, Tian
;
Cornella, Josep
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Cornella, Josep
;
Li, Chao
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Li, Chao
;
Malins, Lara R.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Malins, Lara R.
;
Edwards, Jacob T.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Edwards, Jacob T.
;
Kawamura, Shuhei
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Kawamura, Shuhei
;
Maxwell, Brad D.
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Bristol Myers Squibb Co, Discovery Chem Platforms Radiochem, POB 4000, Princeton, NJ USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Maxwell, Brad D.
;
Eastgate, Martin D.
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Bristol Myers Squibb Co, Chem Dev, One Squibb Dr, New Brunswick, NJ 08903 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Eastgate, Martin D.
;
Baran, Phil S.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Qin, Tian
;
Cornella, Josep
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Cornella, Josep
;
Li, Chao
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Li, Chao
;
Malins, Lara R.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Malins, Lara R.
;
Edwards, Jacob T.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Edwards, Jacob T.
;
Kawamura, Shuhei
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Kawamura, Shuhei
;
Maxwell, Brad D.
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Bristol Myers Squibb Co, Discovery Chem Platforms Radiochem, POB 4000, Princeton, NJ USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Maxwell, Brad D.
;
Eastgate, Martin D.
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Bristol Myers Squibb Co, Chem Dev, One Squibb Dr, New Brunswick, NJ 08903 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
Eastgate, Martin D.
;
Baran, Phil S.
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Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USAScripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA