General and selective metal-free radical α-C–H borylation of aliphatic amines

Sumon Sarkar, Sidhant Wagulde, Xiangqing Jia, Vladimir Gevorgyan

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


Despite recent developments, selective C(sp3)–H borylation of feedstock amines remains a formidable challenge. Herein, we have developed a general, mild, and photoinduced transition-metal- and strong-base-free method for α-C(sp3)–H borylation of amines. This protocol features a regioselective 1,5-hydrogen atom transfer process to access key α-aminoalkyl radical intermediate using commercially available easy-to-install/remove iodobenzoyl radical translocating group. Remarkably, this general, efficient, and operationally simple method allows activation of primary and secondary α-C–H sites of a broad range of acyclic and cyclic amines toward highly regio- and diastereo-selective syntheses of valuable α-aminoboronates. Utility of this protocol has been demonstrated by its employment in late-stage borylation of structurally complex amines and formal C–H arylation reaction of amines. Thus, it is expected that this operationally simple, general, and practical method will find broad application in organic synthesis and drug discovery.

Original languageEnglish (US)
Pages (from-to)3096-3108
Number of pages13
Issue number11
StatePublished - Nov 10 2022


  • amines
  • borylation
  • C–H activation
  • Other
  • photochemistry
  • radicals
  • SDG3: Good health and well-being

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry


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