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CO 2 ‐Controlled Reductive Amination Reactions with NaBH 4
Author(s) -
Petersen Allan R.,
Lauridsen Jerik Mathew Valera,
Lee JiWoong
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001408
Subject(s) - reductive amination , chemistry , iminium , reagent , reactivity (psychology) , reducing agent , alkylation , selectivity , amination , organic chemistry , combinatorial chemistry , ion , catalysis , medicine , alternative medicine , pathology
We report the use of CO 2 to curb the reactivity of NaBH 4 enabling its use in reductive amination reactions. CO 2 readily reacts with NaBH 4 to decrease its capacity to reduce aldehydes to alcohols while remaining able to reduce imines and iminium ions for desired alkylation reactions. The formation of NaBH(OCHO) 3 as a reducing reagent was critical to achieve the desired selectivity. A general protocol was established for C–N bond formation reactions and replacing NaBH 4 with NaBD 4 allowed for reductive amination with concomitant deuteration to be carried out.