Tetrahedron p. 469 - 482 (1993)
Update date:2022-09-26
Topics: Regioselectivity Electron transfer Regioselective preparation Substrate Scope Lithiation Reaction Optimization Functional Group Tolerance Catalytic Process Chloroarenes Organolithium reagent Reactivity study
Guijarro, Albert
Ramon, Diego J.
Yus, Miguel
The lithiation of different functionalized chloroarenes (dichlorobenzenes 1 and 3, mono and dichlorophenols 9 and 14, and chloropivalanilides 18) in the presence of a catalytic amount of naphthalene leads to the corresponding functionalized lithioarenes, which react with electrophiles to give the expected polyfunctionalized aromatic molecules 2, 4, 10, 19, 21, 22 and 24 in a regioselective manner. In the case of starting from chlorinated phenols or anilides a deprotonation of the functional group is carried out prior to the lithiation process; only for 2-chloropivalanilide 18o a coupling reaction leading to 2-n-butylpivalanilide is observed when an excess of n-butyllithium is used in the deprotonation step.
View MoreZibo Widespread International Business Co.,Ltd
Contact:+86-533-5187258
Address:Room 1012, No. 2 flat of Hongtai Building, Songling East Road, Zichuan, Zibo, Shandong, China
Alchemist-pharm chemical Technology Co. Ltd.
website:http://www.alchemist-pharm.com
Contact:0086-371-67991738
Address:Address:No. 35 Dongqing Street High-tech District 450001, Zhengzhou China
Wuhan Better Organic Technology Inc.
Contact:13307163183
Address:Wuhan Economic&Technology Development Zone, Hubei
Shanghai Forever Synthesis Co.,Ltd.
Contact:021-61124658
Address:Zhoukang Road,Pudong New District,Shanghai,China
Weifang Ocean Trading Co., Ltd.
Contact:+86-536-2081155
Address:Room2606, Yuqing Building, 518#, Yuquan Road, High-tech Development Zone, Weifang City, Shandong Province, China
Doi:10.1002/hlca.19920750806
(1992)Doi:10.1002/chem.201503494
(2015)Doi:10.1039/c2nj40468k
(2012)Doi:10.1016/S0040-4039(00)60566-X
(1993)Doi:10.1016/0040-4039(94)88306-8
(1994)Doi:10.1016/S0040-4020(01)85812-9
(1993)