Tetrahedron Letters (2020)
Update date:2022-07-29
Topics: Regioselectivity Mild Reaction Conditions Tolerance of Functional Groups Reducing Agent Substrate Limitations Catalyst Sensitivity Challenging Imine Formation Catalyst Cost Ligand Selection
Nguyen, Dat P.
Sladek, Rudolph N.
Do, Loi H.
The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of <1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).
View MoreHubei Lingsheng Pharmaceuticals Co., Ltd.
Contact:+86-0710-3538058
Address:Xiangyang City Xiangcheng Economic Development Zone, Hubei Province
Contact:0086-357-6662688
Address:Zhaocheng town, Hongtong County, Linfen City, Shanxi Province
website:http://www.china-sinoway.com
Contact:+86-592-5853819
Address:16/F,Huicheng Comm,Complex,No839 XiaHe Rd, Xiamen,China
Hangzhou Maytime Bio-Tech Co.,Ltd.
website:http://www.maytime.com.cn
Contact:+86-571-88925295 88920965
Address:NO.2-1701 Ganghui Central Ningwei Street, Xiaoshan Hangzhou Zhejiang China
Jinan Boss Chemical Industry Co., Ltd.
website:http://www.chemboss.com.cn
Contact:+86-531-58591595
Address:No2.Hualong Road, Jinan, China
Doi:10.1002/ejoc.200300373
(2004)Doi:10.1002/ejic.200300229
(2003)Doi:10.1002/hlca.19370200138
(1937)Doi:10.1021/jo00138a008
(1982)Doi:10.1021/ol070147w
(2007)Doi:10.1016/j.bmc.2011.11.035
(2012)