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Peer-reviewedCC BYACS Catalysis

Cross-Electrophile Coupling of Challenging 5-Membered Heteroaryl Bromides with Alkyl Electrophiles

  • Benjamin N. Ahern1
  • J. Gray Cicmanec1
  • Abigail N. Smith2
  • Rachel K. Chambers2
  • Suhelen Vásquez‐Céspedes2
  • Nicholas P. R. Onuska2
  • Daniel J. Weix1
  1. 1University of Wisconsin-Madison , , 1101 University Ave , , ,
  2. 2Eli Lilly andCompany , , ,
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Abstract

Although alkylated 5-membered heteroarenes are common in pharmaceuticals, there are limited methods to construct them by cross- electrophile coupling. In this report, a systematic study of 5-membered heteroaryl bromides sheds light on an unappreciated reason for this challenge: their relative reactivity spans almost three orders of magnitude and includes examples in the range of aryl iodides and aryl chlorides. By taking this reactivity into consideration, successful conditions were found using PyBCamCN for primary alkyl halides and 4,4'-MeOBpy complexes for secondary alkyl halides (42 examples, 60% average yield).

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Cite

BibTeXRIS
BibTeX
@article{ahern2026crosselectrophile,
  title = {{Cross-Electrophile Coupling of Challenging 5-Membered Heteroaryl Bromides with Alkyl Electrophiles}},
  author = {Benjamin N. Ahern and J. Gray Cicmanec and Abigail N. Smith and Rachel K. Chambers and Suhelen Vásquez‐Céspedes and Nicholas P. R. Onuska and Daniel J. Weix},
  journal = {ACS Catalysis},
  year = {2026},
  month = jun,
  doi = {10.1021/acscatal.6c03034},
  url = {https://doi.org/10.1021/acscatal.6c03034},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Cross-Electrophile Coupling of Challenging 5-Membered Heteroaryl Bromides with Alkyl Electrophiles
AU  - Benjamin N. Ahern
AU  - J. Gray Cicmanec
AU  - Abigail N. Smith
AU  - Rachel K. Chambers
AU  - Suhelen Vásquez‐Céspedes
AU  - Nicholas P. R. Onuska
AU  - Daniel J. Weix
PY  - 2026
DA  - 2026/06/08
JO  - ACS Catalysis
DO  - 10.1021/acscatal.6c03034
UR  - https://doi.org/10.1021/acscatal.6c03034
AB  - Although alkylated 5-membered heteroarenes are common in pharmaceuticals, there are limited methods to construct them by cross- electrophile coupling. In this report, a systematic study of 5-membered heteroaryl bromides sheds light on an unappreciated reason for this challenge: their relative reactivity spans almost three orders of magnitude and includes examples in the range of aryl iodides and aryl chlorides. By taking this reactivity into consideration, successful conditions were found using PyBCamCN for primary alkyl halides and 4,4'-MeOBpy complexes for secondary alkyl halides (42 examples, 60% average yield).
SN  - 2155-5435
ER  -