Palladium-Catalyzed Coupling of Propargylic Carbonates with N-Tosylhydrazones: Highly Selective Synthesis of Substituted Propargylic N-Sulfonylhydrazones and Vinylallenes

• Published in: Chemistry : a European journal Vol. 17; no. 25; pp. 6918 - 6921
• Main Authors: Chen, Zi-Sheng, Duan, Xin-Hua, Wu, Lu-Yong, Ali, Shaukat, Ji, Ke-Gong, Zhou, Ping-Xin, Liu, Xue-Yuan, Liang, Yong-Min
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 14.06.2011; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: allenes; Carbonates; Carbonates - chemistry; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; cross-coupling; Hydrazones - chemical synthesis; Hydrazones - chemistry; Joining; Molecular Structure; N-tosylhydrazones; palladium; Palladium - chemistry; Pargyline - chemical synthesis; Pargyline - chemistry; Physical Sciences; propargylic substitution; Science & Technology; Synthesis; Tosyl Compounds - chemistry; Vinyl Compounds - chemical synthesis; Vinyl Compounds - chemistry; ALPHA-DIAZOCARBONYL COMPOUNDS; ORGANIC-SYNTHESIS; BENZYL BROMIDES; NUCLEOPHILIC-SUBSTITUTION; COMPLEXES; allenes; ALLYL HALIDES; AMINATION; N-tosylhydrazones; ARYL HALIDES; ESTERS; cross-coupling; propargylic substitution; palladium
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201100248

An efficient palladium‐catalyzed coupling of propargylic carbonates (1) with N‐tosylhydrazones (2, 2′) has been carried out. A wide range of propargylic N‐sulfonylhydrazones (3) and multisubstituted vinylallenes (4) can be obtained selectively by using either [PdCl2(CH3CN)2] or [Pd2(dba)3] as catalysts. (dba=trans,trans‐dibenzylideneacetone, dppp=propane‐l,3‐diylbis(diphenylphosphane), Ts=4‐toluenesulfonyl.)