Herein,we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid(HCl)and N-chlorosuccinimide(NCS),which is significantly different from conventional mig...Herein,we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid(HCl)and N-chlorosuccinimide(NCS),which is significantly different from conventional migration modes under basic conditions.In this protocol,HCl,as the first electrophile,activates the C≡C bond,triggering the first 1,2-aryl migration.Subsequently,NCS promotes a secondary metallate shift,enabling the construction of polysubstituted alkenes.Notably,this process can work well under mild conditions,exhibits high efficiency,and provides valuable products.This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions,it can proceed smoothly under acidic conditions as well,which greatly expands the scope of this well-known olefination reaction.展开更多
基金the financial support from the National Key Research&Development Program of China(2023YFF0723900)the National Natural Science Foundation of China(22271105)+3 种基金the Natural Science Foundation of Fujian Province(2022J02009)the Open Research Fund of State Key Laboratory of Coordination ChemistrySchool of Chemistry and Chemical Engineering,Nanjing Universitythe Hubei Key Laboratory of Pollutant Analysis&Reuse Technology Open Foundation(PA240102)。
文摘Herein,we report a distinctive and marvelous dual-migration of alkynyl tetracoordinate borons activated by both hydrochloric acid(HCl)and N-chlorosuccinimide(NCS),which is significantly different from conventional migration modes under basic conditions.In this protocol,HCl,as the first electrophile,activates the C≡C bond,triggering the first 1,2-aryl migration.Subsequently,NCS promotes a secondary metallate shift,enabling the construction of polysubstituted alkenes.Notably,this process can work well under mild conditions,exhibits high efficiency,and provides valuable products.This transformation reveals that Zweifel olefination is not just limited to traditional basic conditions,it can proceed smoothly under acidic conditions as well,which greatly expands the scope of this well-known olefination reaction.
