Gram-scale nucleophilic aromatic substitution of 4,7-dibromo-5,6-difluoro-[2,1,3]-benzothiadiazole for Synthesis of 4,7-dibromo-5,6-BINOL-O-benzo[2,1,3]thiadiazole, and 4,7-dibromo-5,6-dicarbazol-N-ylbenzo[2,1,3]thiadiazole. The Stille coupling reaction and continuous Heck coupling reaction for synthesis of 4,7-bispara-chlorophenyl-5,6-dicarbazol-N-ylbenzo[2,1,3]thiadiazole

Nguyen Van Gioi; Nguyen Dinh Ngoc; Pham Thi Thu Trang; Phung Thi Mai; Ta Hong Duc; Tran Thuong Quang; Thi Phuong Ly GIANG; Dang Thanh Tung

doi:10.62239/jca.2025.065

Authors

Nguyen Van Gioi School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Nguyen Dinh Ngoc School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Pham Thi Thu Trang School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Phung Thi Mai School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Ta Hong Duc School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Tran Thuong Quang School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Giang Thi Phuong Ly School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM
Dang Thanh Tung School of Chemistry and Life Science, Hanoi University of Science and Technology, 1 Dai Co Viet Road, Hanoi, VIETNAM

DOI:

https://doi.org/10.62239/jca.2025.065

Keywords:

FeS2, g-C3N4, anode, lithium-ion battery

Abstract

In this study, we delveloped a simple and efficient synthetic procedure for the nucleophilic substitution of 4,7-dibromo-5,6-diflourobenzo[2,1,3]thiadiazole with diols, diamines and carbazole to obtain 4,7-dibromo-5,6-dinucleophile-benzo[2,1,3]diadiazole derivatives. The chiral version of BINOL and BINAM, based on (R-/S-) atropisomers of binaphthyl, were employed as nucleophilic reagents under bases (DBU 1,8-diazabicyclo[5.4.0]undec-7-ene and/or K2CO3). The nucleophillic carbazol-N-yl sodium species were synthesized via recrystallized and subsequent treatment in dried DMF and in the presence of strong base as NaH. All three nucleophiles participated successfully in the SnAr reaction, affording excellent yields with BINAM and quantitative yields with carbazole and BINOL.

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