Peroxides as “Switches” of Dialkyl H‑Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2‑Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates

Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The dialkyl H-phosphonate (RO)2P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)2P...

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Published inJournal of organic chemistry Vol. 79; no. 17; pp. 8407 - 8416
Main Authors Chen, Xiao-Lan, Li, Xu, Qu, Ling-Bo, Tang, Yu-Chun, Mai, Wen-Peng, Wei, Dong-Hui, Bi, Wen-Zhu, Duan, Li-Kun, Sun, Kai, Chen, Jian-Yu, Ke, Dian-Dian, Zhao, Yu-Fen
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.09.2014
Amer Chemical Soc
Subjects
Benzothiazoles - chemical synthesis
Benzothiazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic
Metals
Molecular Structure
Organophosphonates - chemistry
Peroxides - chemistry
Physical Sciences
Science & Technology
DESIGN
ACID
BIOLOGICAL EVALUATION
ARYL
INHIBITORS
TRANSFORMYLASE
ALKYNES
DERIVATIVES
BENZOTHIAZOLES
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Summary:Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The dialkyl H-phosphonate (RO)2P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)2POH. TBHP triggered α-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C2-acylation of benzothiazoles and C2-phosphonation of benzothiazoles.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo501791n