posted on 2021-08-20, 10:29authored byShihui Luo, Chaoqun Weng, Zixuan Qin, Ke Li, Tianxiao Zhao, Yuxuan Ding, Chen Ling, Yuan Ma, Jie An
α,β-Deuterated amines
are crucial for the development
of deuterated drugs. We intend to introduce the novel tandem H/D exchange-single
electron transfer (SET) reductive deuteration strategy with high pot-
and reagent-economy by the synthesis of α,β-deuterated
amine using nitrile as the precursor. The H/D exchange of the −CH2CN group was achieved by D2O/Et3N, which
were also the required reagents in the tandem SmI2-mediated
SET reductive deuteration of the α-deuterated nitrile. The potential
application of this method was further showcased by the synthesis
of bevantolol-d4.