4.6 Article

Transition-metal-free C-S, C-Se, and C-Te Bond Formation from Organoboron Compounds

Journal

CHEMICAL RECORD
Volume 21, Issue 10, Pages 2855-2879

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100021

Keywords

Alternative sources of energy; Boron reagent; Clean procedures; Chalcogenide; Transition-metal-free

Funding

  1. Brazilian agency CNPq
  2. Brazilian agency FAPERGS [PRONEM 16/2551-0000240-1]
  3. CNPq
  4. CoordenacAo de Aperfeicoamento de Pessoal de Nivel Superior-Brasil (CAPES) [001]

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This review discusses the successful applications of organoboron compounds in transition-metal-free C-S, C-Se, and C-Te bond formations. Various methods, including conventional heating and alternative energy sources, were used to synthesize functionalized chalcogenides with high molecular diversity. The studies and proposed mechanisms also highlighted the reuse of reaction promoters in these processes.
The present review describes the successful application of organoboron compounds in transition-metal-free C-S, C-Se, and C-Te bond formations. We presented studies regarding these C-Chalcogen bond formations using organoboron reagents, such as boronic acids, boronic esters, borate anions, and several sources of chalcogen atoms/moieties. Moreover, a broad range of transition-metal-free approaches to synthesize sulfides, selenides, and tellurides were described using conventional heating methods, which are sometimes green since they use green solvents, safe reagents, among others. Furthermore, protocols using alternative energy sources, including ultrasound, microwave irradiation, photocatalysis, and electrolytic processes, were also shown to be suitable. These protocols were applied to prepare a broad scope of functionalized chalcogenides with high molecular diversity. These studies and their proposed mechanisms were also reported herein in addition to the reuse of reaction promoters.

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