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PreprintCC BYChemRxiv

A General Approach to Highly Substituted 1,2-Azaborines via Borylative Benzannulation of Unsaturated Imines

  • Zhongming Cheng1,2
  • Masanori Hirao1,2
  • Yao Ge1,2
  • Liyan Kan1,2
  • Kangmin Wen1,2
  • Qiang Yang3,4
  • Youming Huang3,4
  • Jiang Wang3,4
  • Renato A. Bauer3,4
  • Guangbin Dong1,2
4 affiliations
  1. 1Chemistry
  2. 2The University of Chicago
  3. 3Lilly Research Laboratories,
  4. 4Eli Lilly and Company
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Abstract

Highly substituted, monocyclic 1,2-azaborines could expand the chemical space available for benzene bioisosterism; however, their synthesis remains an unmet challenge. Here we report a general, modular, transition-metal-free strategy that couples unsaturated imines with dihaloboranes to construct diverse 1,2-azaborines through a borylative benzannulation pathway. This method provides efficient access to tetra-, penta-, and hexa-substituted azaborines, including fused, macrocyclic and heteroatom-substituted scaffolds. High chemoselectivity and convenient handling are achieved by developing well-defined quinoline-buffered borylation reagents. Post-functionalization at the boron and nitrogen positions of 1,2-azaborines, synthesis of a BN-isostere of xibornol, and access to isotopically enriched 10B-1,2-azaborines have been demonstrated.

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Cite

BibTeXRIS
BibTeX
@misc{cheng2026general,
  title = {{A General Approach to Highly Substituted 1,2-Azaborines via Borylative Benzannulation of Unsaturated Imines}},
  author = {Zhongming Cheng and Masanori Hirao and Yao Ge and Liyan Kan and Kangmin Wen and Qiang Yang and Youming Huang and Jiang Wang and Renato A. Bauer and Guangbin Dong},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008294/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008294/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - A General Approach to Highly Substituted 1,2-Azaborines via Borylative Benzannulation of Unsaturated Imines
AU  - Zhongming Cheng
AU  - Masanori Hirao
AU  - Yao Ge
AU  - Liyan Kan
AU  - Kangmin Wen
AU  - Qiang Yang
AU  - Youming Huang
AU  - Jiang Wang
AU  - Renato A. Bauer
AU  - Guangbin Dong
PY  - 2026
DA  - 2026/09/04
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008294/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008294/v1
AB  - Highly substituted, monocyclic 1,2-azaborines could expand the chemical space available for benzene bioisosterism; however, their synthesis remains an unmet challenge. Here we report a general, modular, transition-metal-free strategy that couples unsaturated imines with dihaloboranes to construct diverse 1,2-azaborines through a borylative benzannulation pathway. This method provides efficient access to tetra-, penta-, and hexa-substituted azaborines, including fused, macrocyclic and heteroatom-substituted scaffolds. High chemoselectivity and convenient handling are achieved by developing well-defined quinoline-buffered borylation reagents. Post-functionalization at the boron and nitrogen positions of 1,2-azaborines, synthesis of a BN-isostere of xibornol, and access to isotopically enriched 10B-1,2-azaborines have been demonstrated.
ER  -