Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 73-93Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02322
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Funding
- DST-SERB [SB/S1/OC-47/2014]
- CSIR, New Delhi, India [02(0185)/13/EMRII]
- CSIR
- IITM
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Oxidative C-C coupling of carbazoles possessing various substituents is demonstrated in the presence of organic (metal-free) recyclable oxidants, such as DDQ or CA/H+, for accessing bicarbazole regioisomers. Differently substituted carbazoles are examined to showcase regioselective discrimination (3,3'- versus 1,3'-bicarbazoles) and preferences based on sterics and electronics in oxidative coupling. Finally, a mechanism that involves the carbazole radical cation has been traced (evidenced) and proposed on the basis of the UV-vis-NIR absorption and EPR spectroscopy results. This study underlines the strategic chemical preparation of a series of bicarbazoles in an efficient manner.
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