Chemo- and regioselective nucleophilichydrofunctionalization of unactivated aliphaticalkenes under transition-metal-free catalysts

Ying Zhan,^{‡ a}Yao Zhao,^{‡ a}Qiang Du,^aJiacheng Rui,^aRizhi Chen,^bXintao Zheng^aandXiaojin Wu^*a

^aInstitute of Advanced Synthesis, School of Chemistry and Molecular Engineering,Nanjing Tech University, Nanjing 211816, China.

^bState Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing TechUniversity, Nanjing 211816, China

Abstract:Transition-metal-free-catalyzed nucleophilic hydrofunctionalization of both terminal and internal unactivated aliphatic alkenes hasbeen described for the first time. Most topical classes of carbon,nitrogen and oxygen nucleophiles are well-compatible. The highlychemoselective unprotected dinucleophiles are also presented inthe atom-economical approach. More than 80 structurallycomplex β-hetero-substituted aliphatic amides were rapidly synthesized in good yield with exclusive Markovnikov selectivity,which are difficult to be achieved efficiently by the traditionalMichael addition of conjugated amides due to their poor intrinsicelectrophilicity.

Green Chem.,2021, 23,3250–3255(IF = 10.182).

文章链接：https://doi.org/10.1039/D1GC00474C