Advanced Synthesis and Catalysis p. 166 - 176 (2020)
Update date:2022-08-11
Topics:
Korvinson, Kirill A.
Akula, Hari K.
Malinchak, Casina T.
Sebastian, Dellamol
Wei, Wei
Khandaker, Tashrique A.
Andrzejewska, Magdalena R.
Zajc, Barbara
Lakshman, Mahesh K.
Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).
View MoreZHEJIANG JIANYE CHEMICAL CO.,LTD.
Contact:86-571-64149273,64149234
Address:No. 48, Fuxi Road, Meicheng Town
Changzhou Sunlight Pharmaceutical Co., Ltd.
Contact:+86-519-83131668;83139028;83138042;83137041
Address:JiuliStreet, Benniu Town Changzhou City, Jiangsu Province
NIGNXIA XINDACHANG TECHNOLOGY CO.,LTD
website:https://xdcchemical.com/
Contact:86-311-85758226
Address:North Industry Area, Wuji
ALPHA PHARMACEUTICAL CO,LTD JIANGSU
Contact:+86-527-84829968,+86-527-84829998
Address:suqian city
GUANGZHOU MEDCAN PHARMATECH LTD
website:http://www.gzmedcan.com
Contact:+86-20-82519649
Address:Building J,Room 101,1 JiangtashanRd,Guang Zhou Science City,Guang Zhou ,China
Doi:10.1021/jo01163a020
(1948)Doi:10.1134/S1070427211090023
(2011)Doi:10.1038/168996b0
(1951)Doi:10.1039/b713925j
(2008)Doi:10.1111/jphp.12573
(2016)Doi:10.1021/ic50026a023
(1965)