CO 2 ‐Controlled Reductive Amination Reactions with NaBH 4 | Zendy

Petersen Allan R. | Zendy; Lauridsen Jerik Mathew Valera | Zendy; Lee JiWoong | Zendy

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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.

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