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Rh(III)-catalysed C-H/C-H cross-coupling of -aryl sulfoximines with thiophenes: facile access to [1]benzothieno[3,2-][1]benzothiophene (BTBT) and benzothiazines. | LitMetric

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

Chem Commun (Camb)

Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

Published: July 2022

AI Article Synopsis

  • This study presents a method for creating complex organic compounds using rhodium-catalyzed reactions of sulfoximines and thiophenes, employing a chelation-assisted strategy.
  • The process effectively produces compounds like [1]benzothieno[3,2-][1]benzothiophene (BTBT) and benzothiazine, demonstrating good compatibility with halogen substituents for further chemical transformations.
  • The benzothiazine derivative generated exhibits a deep blue fluorescence with notable brightness, specific color coordinates, and a prolonged fluorescence lifetime.

Article Abstract

Reported herein is rhodium-catalysed oxidative C-H/C-H cross-coupling of -aryl sulfoximines with thiophenes a chelation-assisted strategy, which provides an efficient approach for the construction of [1]benzothieno[3,2-][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.

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Source
http://dx.doi.org/10.1039/d2cc02232jDOI Listing

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