Journal of Organic Chemistry p. 1594 - 1603 (1984)
Update date:2022-08-03
Topics:
Beadle, James R.
Korzeniowsky, Stephen H.
Rosenberg, David E.
Garcia-Slanga, Blanche J.
Gokel, George W.
Two problems have hindered the Gomberg-Bachmann (GB) and Pschorr reactions of arenediazonium cations: the instability of the arenediazonium salts and side reactions.Arenediazonium tetrafluoroborate and hexafluorophosphate salts can be prepared in high yield and purity and can be stored safely.Unfortunately, these salts are insoluble in most nonpolar organic solvents.Crown ether complexation or other phase-transfer (pt) catalytic methodology can ameliorate this situation, and reactions conducted by the approaches outlined herein often afforded coupling or cyclization products in high yield and corresponding purity.The use of crown ethers, quarternary 'onium salts, lipophilic carboxylic acid salts, and even the polar cosolvent acetonitrile increase the utility of the ptGB reaction dramatically.Sixty examples of couplings are reported along with an assessment of selectivities.A number of examples are also presented of phase-transfer-type Pschorr cyclizations.In the latter case, the use of potassium superoxide, KO2, is introduced to suppress indazole formation.
View MoreChengdu Sino-Strong Pharmaceutical Co.,Ltd.
website:http://www.sino-strong.com.cn
Contact:+86-28-82666753
Address:459 West haike road,Cross-straits technological industry park, Wenjiang district,Chengdu, P.R.China
Xiamen Hisunny Chemical Co.,Ltd
website:http://www.hisunnychem.com
Contact:+86-592-3327115
Address:Unit 603,No.879,Xiahe Road,Meixin Building,Xiamen,China
Contact:+86-710-3516804
Address:Number 83,Panggong road,Xiangcheng District,Xiangyang ,Hubei
Contact:+86-025-52406782
Address:8 Taizishan Rd., Yanjiang Industrial Development Area, Nanjing, Jiangsu, China.
Hubei Xinghuo Chemical Co., Ltd.,
Contact:13925817279 13907299441
Address:Xinghuo Fine Chemistry Industrial Park, Xiaochang County, Hubei Province, China
Doi:10.1021/np2007878
(2012)Doi:10.1007/BF01186251
(1992)Doi:10.1016/j.tetlet.2011.12.044
(2012)Doi:10.1021/acs.orglett.7b00813
(2017)Doi:10.1039/c1dt11546d
(2012)Doi:10.1016/0031-9422(88)84080-9
(1988)