Rh( iii )-catalysed C–H/C–H cross-coupling of S -aryl sulfoximines with thiophenes: facile access to [1]benzothieno[3,2- b ][1]benzothiophene (BTBT) and benzothiazines

Reported herein is rhodium-catalysed oxidative C–H/C–H cross-coupling of S -aryl sulfoximines with thiophenes via a chelation-assisted strategy, which provides an efficient approach for the construction of [1]benzothieno[3,2- b ][1]benzothiophene (BTBT) and benzothiazine skeletons from easily availa...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-07, Vol.58 (57), p.7952-7955
Main Authors: Yang, Chengyong, Liu, Zheng, Cheng, Rui, Du, Jiping, Ran, Chunhao, Wu, Di, Lan, Jingbo
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzothiophene
Catalysis
Chelation
Coupling (molecular)
Cross coupling
Rhodium
Substrates
Thiophenes
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Summary:Reported herein is rhodium-catalysed oxidative C–H/C–H cross-coupling of S -aryl sulfoximines with thiophenes via a chelation-assisted strategy, which provides an efficient approach for the construction of [1]benzothieno[3,2- b ][1]benzothiophene (BTBT) and benzothiazine skeletons from easily available substrates. This protocol exhibits a good compatibility with halogen substituents, thus paving the way for further transformation to prepare various organic functional molecules. The resulting benzothiazine derivative shows a deep blue emission with Commission Internationale de ’Eclairage (CIE) coordinates of (0.15, 0.04), a high quantum yield, and a delayed fluorescence lifetime.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc02232j