Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines

• Published in: European journal of organic chemistry Vol. 2013; no. 31; pp. 7175 - 7183
• Main Authors: Quan, Zheng-Jun, Jing, Fu-Qiang, Zhang, Zhang, Da, Yu-Xia, Wang, Xi-Cun
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.11.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkynes; C-C cou­pling; Chemical reactions; Chemistry; Chemistry, Organic; Cross coupling; Nitrogen heterocycles; Palladium; Physical Sciences; Pyridines; Pyrimidines; Science & Technology; Sulfonates; Synthetic methods; C-C coupling; PHASE SYNTHESIS; BIGINELLI 3,4-DIHYDROPYRIMIDIN-2(1H)-ONE; SOLID-PHASE; Palladium; ARYL IMIDAZOLYLSULFONATES; CALCIUM-CHANNEL BLOCKERS; SUZUKI-MIYAURA; ARYLBORONIC ACIDS; BORONIC ACIDS; Cross-coupling; Nitrogen heterocycles; Synthetic methods; CARBON-CARBON; SONOGASHIRA REACTIONS; Alkynes
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201300592

Pyrimidin‐2‐yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross‐coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2‐catalyzed Suzuki and Sonogashira reactions. A wide array of C2‐functionalized pyrimidines have been prepared in good to excellent yields. 2‐Arylpyridines and 2‐(oct‐1‐ynyl)pyridine were also synthesized. An efficient means to synthesize expanded pyrimidin‐2‐yl conjugated systems was developed by using Pd(OAc)2‐catalyzed cross‐coupling reaction of pyrimidin/pyridin‐2‐yl sulfonates with arylboronic acids and terminal alkynes. Compared with 2‐chloropyrimidines, pyrimidin‐2‐yl sulfonates can be easily prepared from inexpensive commercial materials and the reactions are more efficient.