Chemo- and regioselective nucleophilic hydrofunctionalization of unactivated aliphatic alkenes under transition-metal-free catalysts

Ying Zhan,^{‡ a} Yao Zhao,^{‡ a} Qiang Du, ^a Jiacheng Rui, ^a Rizhi Chen, ^b Xintao Zheng ^a and Xiaojin 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 Tech University, Nanjing 211816, China

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

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

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