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C-H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr3.
Wu, Gaorong; Fu, Xiaopan; Wang, Yangyang; Deng, Kezuan; Zhang, Lili; Ma, Tao; Ji, Yafei.
Affiliation
  • Wu G; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
  • Fu X; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
  • Wang Y; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
  • Deng K; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
  • Zhang L; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
  • Ma T; School of Chinese Materia Medica, Beijing University of Chinese Medicine, Liangxiang Campus, Fangshan District, Beijing 102488, P. R. China.
  • Ji Y; Engineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.
Org Lett ; 22(17): 7003-7007, 2020 09 04.
Article in En | MEDLINE | ID: mdl-32820932
ABSTRACT
A method for ortho-C-H borylation of diphenylamines using BBr3 as the boron source has been reported. The noncatalytic adamantane-1-carbonyl directed reaction exhibited site exclusivity and good functional group tolerance. Generally, the borylation occurred at the more electron-rich aromatic ring and the borylated products could be converted to various useful intermediates. Besides, the derived arylation and removal of auxiliary of the product could be achieved in a one-pot fashion.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article