Sodium Hypophosphite as a Bulk and Environmentally Friendly Reducing Agent in the Reductive Amination

Fedor Kliuev; Anton Kuznetsov; Oleg I Afanasyev; Sofiya A Runikhina; Ekaterina Kuchuk; Evgeniya Podyacheva; Alexey A Tsygankov; Denis Chusov

doi:10.1021/acs.orglett.2c02807

Sodium Hypophosphite as a Bulk and Environmentally Friendly Reducing Agent in the Reductive Amination

Org Lett. 2022 Oct 28;24(42):7717-7721. doi: 10.1021/acs.orglett.2c02807. Epub 2022 Oct 14.

Authors

Fedor Kliuev^{1

2}, Anton Kuznetsov³, Oleg I Afanasyev¹, Sofiya A Runikhina¹, Ekaterina Kuchuk¹, Evgeniya Podyacheva^{1

2}, Alexey A Tsygankov¹, Denis Chusov^{1

4}

Affiliations

¹ A.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow 119991, Russian Federation.
² National Research University Higher School of Economics, Moscow 101000, Russian Federation.
³ Moscow South-Eastern School named after V.I. Chuikov (Moscow Chemical Lyceum), Tamozhenniy proezd 4, Moscow 111033, Russian Federation.
⁴ Russian Federation; Plekhanov Russian University of Economics, Stremyanny lane 36, Moscow 117997, Russian Federation.

PMID: 36240121
DOI: 10.1021/acs.orglett.2c02807

Abstract

NaH₂PO₂ was found to promote reductive amination. Being nontoxic, stable, environmentally benign, and available in bulk amounts, this reducing agent showed a powerful potential to compete with classical reductants applied in the target process. An E factor of 1 was achieved for the substrate scope. Different carbonyl compounds reacted with amines under the developed conditions. The reaction demonstrated a great compatibility with a wide range of functional groups. Reaction conditions were scaled up to 200-fold.