Cross-Coupling of N-Allylic Sulfonimides with Organozinc Reagents at Room Temperature

• Published in: European journal of organic chemistry Vol. 2012; no. 22; pp. 4107 - 4109
• Main Authors: Tang, Xiang-Ling, Wu, Zhao, Li, Man-Bo, Gu, Yonghong, Tian, Shi-Kai
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-08-2012; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Alkenes; Chemistry; Cross-cou­pling; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Palladium; Preparations and properties; Sulfur; Zinc; Zinc Organic compounds; Chemical reagent; Ether; Alkenes; Transition metal; Palladium; Selectivity; Allylic compound; Organic sulfide; Zinc; Chemical coupling; Ester; Alkene; Cross-coupling; Benzylic compound; Cross reaction; Sulfur; Platinoid; Ethylenic compound; Room temperature
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200594

An efficient cross‐coupling reaction of N‐allylic sulfonimides with organozinc reagents has been developed. In the presence of 1 mol‐% of Pd2(dba)3, a range of N‐allylic sulfonimides smoothly couple with various organozinc reagents at room temperature to give the corresponding (E)‐alkene products in moderate to excellent yields and with good to exclusive α‐selectivity. It is noteworthy that allyl ether, benzyl ether, and ester are tolerated under the reaction conditions.
A range of N‐allylic sulfonimides smoothly couple with various organozinc reagents in the presence of 1 mol‐% of Pd2(dba)3 at room temperature to give the corresponding (E)‐alkene products in moderate to excellent yields and with good to exclusive α‐selectivity.