Expedient Cyano-hydroxylation of Alkenes Enabled by Halogen Atom Transfer Induced Radical Ring-Opening Elaboration of 3-Bromo-isoxazoline Cycloadducts
Hui Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
These authors contributed equally to this work.
Search for more papers by this authorQing Chen
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
These authors contributed equally to this work.
Search for more papers by this authorShuhui Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorCorresponding Author
Cheng-Qiang Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chao Feng
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
State Key Laboratory of Material-Oriented Chemical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
E-mail: [email protected]; [email protected]Search for more papers by this authorHui Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
These authors contributed equally to this work.
Search for more papers by this authorQing Chen
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
These authors contributed equally to this work.
Search for more papers by this authorShuhui Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
Search for more papers by this authorCorresponding Author
Cheng-Qiang Wang
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Chao Feng
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
State Key Laboratory of Material-Oriented Chemical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing, Jiangsu, 211816 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Herein, we present a highly efficient one-pot, two-step synthesis of β-hydroxy nitrile scaffolds, which possess both significant synthetic value and notable biological activity, starting from readily accessible alkenes. This methodology relies crucially on the seamless integration of a highly regioselective (3+2) cycloaddition reaction, employing the commercially available 1,1-dibromoformaldoxime as the 1,3-dipole precursor, with a subsequent halogen atom transfer-induced radical ring-opening elaboration of the resulting 3-bromo-2-isoxazoline cycloadducts. This protocol is featured by mild reaction conditions, broad alkene scope and various derivatizations of the obtained cyano-hydroxylation products, offering a versatile and practical pathway to accessing multi-functionalized molecules.
Supporting Information
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