Advanced Synthesis and Catalysis p. 3359 - 3364 (2015)
Update date:2022-08-05
Topics:
Domingo, Victoriano
Prieto, Consuelo
Castillo, Alexis
Silva, Lucia
Quílez Del Moral, José F.
Barrero, Alejandro F.
We describe efficient procedures based on the use of iodine for the synthesis of biaryls from arylcyclohexenols or arylcyclohexanols using sub-stoichiometric/catalytic iodine and dimethyl sulfoxide (DMSO) as oxidant. Heteroarylcyclohexanols also produced the corresponding biaryl products. It was proven that biphenyl can also be efficiently obtained when the quantity of iodine was reduced to 0.05 equiv. The method is compatible with different functional groups in the aromatic ring (either electron-donating or electron-withdrawing groups). For substrate scope, apart from cyclohexanone and cyclohexenone, some substituted cyclohexanones were also used to synthesize the starting arylcyclohexanols. The process was applied to the synthesis of oligo p-phenylenes and A-ring aromatized steroids, where the combined use of I2/DMSO not only provoked the necessary migration of the methyl group at C-10, but also further extended the conjugation.
View MoreQINGDAO DEVELOP chemistry Co.,Limited
Contact:+86-532-85807910
Address:98#Nanjing Road, Qingdao, China 266071
Suzhou HeChuang Chemical Co.,Ltd.
Contact:+86-512-88800520
Address:No.9 Guanchao Rd,Changshu Advanced Materials Industy Park
Contact:+86-574-87065746
Address:10th Floor, No.787 Baizhang East Road,
Hangzhou LINGEBA Technology Co., Ltd.
Contact:+0086-571-87389059
Address:Office 1-913,NewYouth Plaza, GongShu Area, HangZhou,ZheJiang,P.R.China
Taizhou Chemedir Biopharm-tech Co., Ltd
Contact:+86 523 86200218
Address:G09, No. 1 Avenue China Medical City, Taizhou,Jiangsu, China
Doi:10.1021/ja903967z
(2009)Doi:10.1002/chem.200802654
(2009)Doi:10.1246/bcsj.61.1231
(1988)Doi:10.1016/j.jorganchem.2009.04.002
(2009)Doi:10.1002/anie.201800973
(2018)Doi:10.1016/j.ica.2009.03.048
(2009)