Pd-NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of 2-Pyridyl Ammonium Salts by N-C Activation: Application to the Discovery of Agrochemical Molecular Hybrids

Yanqing Gao; Yuge Hu; Jiuhui Ye; Zhiqing Ma; Juntao Feng; Xili Liu; Peng Lei; Michal Szostak

doi:10.1021/acs.orglett.4c00549

Pd-NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of 2-Pyridyl Ammonium Salts by N-C Activation: Application to the Discovery of Agrochemical Molecular Hybrids

Org Lett. 2024 Mar 22;26(11):2309-2314. doi: 10.1021/acs.orglett.4c00549. Epub 2024 Mar 11.

Authors

Yanqing Gao¹, Yuge Hu¹, Jiuhui Ye¹, Zhiqing Ma^{1

2}, Juntao Feng^{1

2}, Xili Liu^{1

3}, Peng Lei^{1

2

3}, Michal Szostak⁴

Affiliations

¹ Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, China.
² Shaanxi Research Center of Biopesticide Engineering & Technology, Northwest A&F University, Yangling, Shaanxi 712100, China.
³ State Key Laboratory for Crop Stress Resistance and High-Efficiency Production, Northwest A&F University, Yangling, Shaanxi 712100, China.
⁴ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

PMID: 38466078
DOI: 10.1021/acs.orglett.4c00549

Abstract

2-Alkylpyridines are a privileged scaffold throughout the realm of organic synthesis and play a key role in natural products, pharmaceuticals, and agrochemicals. Herein, we report the first B-alkyl Suzuki cross-coupling of 2-pyridyl ammonium salts to access functionalized 2-alkylpyridines. The use of well-defined, operationally simple Pd-NHCs permits for an exceptionally broad scope of the challenging B-alkyl C-N cross-coupling with organoboranes containing β-hydrogen, representing a novel method for the discovery of highly sought-after molecules for plant protection.