Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 8407-8416Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501791n
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Funding
- National Natural Science Foundation of China [21072178]
- Innovation Specialist Projects of Henan Province [114200510023]
- Technology and Science talent Cultivation Project in Zhengzhou City [112PLJRC359]
- Special Fund for the Doctoral Program of Higher Education [20124101110003]
- Foundational and Frontier Technology Research Foundation of Henan Province [132300410027]
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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 diallcyl H-phosphonate (RO)(2)P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)(2)POH. TBHP triggered alpha-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 C-2-acylation of benzothiazoles and C-2-phosphonation of benzothiazoles.
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