TY - JOUR
T1 - Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
AU - Utsumi, Tatsuki
AU - Noda, Kenta
AU - Kawauchi, Daichi
AU - Ueda, Hirofumi
AU - Tokuyama, Hidetoshi
N1 - Funding Information:
This work was supported by JSPS KAKENHI (JP18H04231in Precisely Designed Catalysts with Customized Scaffolding and JP18H04642in Hybrid Catalysis, a Grant-in aid for Scientific Research (B) (18H02549) and (C) (17 K08204)).
Funding Information:
This work was supported by JSPS KAKENHI (JP18H04231in Precisely Designed Catalysts with Customized Scaffolding and JP18H04642in Hybrid Catalysis, a Grant‐in aid for Scientific Research (B) (18H02549) and (C) (17 K08204)).
PY - 2020/9/8
Y1 - 2020/9/8
N2 - Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
AB - Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
KW - Grubbs catalyst
KW - aerobic oxidation
KW - aldehyde
KW - amine
KW - nitrile
UR - http://www.scopus.com/inward/record.url?scp=85088818940&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85088818940&partnerID=8YFLogxK
U2 - 10.1002/adsc.202000663
DO - 10.1002/adsc.202000663
M3 - Article
AN - SCOPUS:85088818940
VL - 362
SP - 3583
EP - 3588
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 17
ER -