Palladium-Catalyzed Sonogashira Coupling Reaction of 2-Amino-3-Bromopyridines with Terminal Alkynes - Modern Research in Catalysis

MRC > Vol.6 No.3, July 2017

Modern Research in Catalysis

Volume 6, Issue 3 (July 2017)

ISSN Print: 2168-4480 ISSN Online: 2168-4499

Google-based Impact Factor: 1.29 Citations

Palladium-Catalyzed Sonogashira Coupling Reaction of 2-Amino-3-Bromopyridines with Terminal Alkynes ()

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DOI: 10.4236/mrc.2017.63009 2,684 Downloads 7,300 Views Citations

Author(s)

Qing Zhu, Lichun Liao, Guo Cheng, Wen Yang, Yingying Deng, Dingqiao Yang^*

Affiliation(s)

Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, China.

ABSTRACT

Palladium-catalyzed the Sonogashira coupling reaction of 3-halogen-2-aminopyridines 1 with terminal alkynes 2 afforded the corresponding 21 target products 3a-3u in the presence of palladium catalyst. The structure of target products 3a-3u was confirmed and characterized by ¹H NMR, ¹³C NMR, and HRMS. The influences of different kinds of catalyst loading, bases, substrates and temperature were also investigated. Under the optimized conditions, including 2.5 mol% Pd (CF₃COO)₂, 5 mol% PPh₃ and 5 mol% CuI as additive, 1 mL Et₃N, substrate 1 with terminal alkynes 2 for the cross-coupling reactions at 100°C for 3 h in DMF afforded the corresponding products of 2-amino-3-alkynylpyridines 3 in moderate to excellent yields (72% - 96%). The present methodology has provided an effective synthetic method including operational convenience, high efficiency and wide-application.

KEYWORDS

Palladium Catalyst, 2-Amino-3-Bromopyridines, Terminal Alkynes, Sonogashira Coupling Reaction

Share and Cite:

Zhu, Q. , Liao, L. , Cheng, G. , Yang, W. , Deng, Y. and Yang, D. (2017) Palladium-Catalyzed Sonogashira Coupling Reaction of 2-Amino-3-Bromopyridines with Terminal Alkynes. Modern Research in Catalysis, 6, 121-133. doi: 10.4236/mrc.2017.63009.

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