Reduction of alkyl and vinyl sulfonates using the CuCl2·2H2O-Li-DTBB(cat.) system |
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| Authors: | Gabriel Radivoy Francisco Alonso Cristian Vitale |
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| Institution: | a Departamento de Química, Instituto de Investigaciones en Química Orgánica (INIQO), Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina
b Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain |
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| Abstract: | The reduction of a series of alkyl mesylates, dimesylates and triflates to the corresponding hydrocarbons was efficiently performed using a reducing system composed of CuCl2·2H2O, an excess of lithium sand and a catalytic amount (5 mol%) of 4,4′-di-tert-butylbiphenyl (DTBB), in tetrahydrofuran at room temperature. The process was also applied to enol and dienol triflates affording alkenes and dienes, respectively. The use of the deuterated copper salt CuCl2·2D2O allowed the simple preparation of the corresponding deuterated products. |
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| Keywords: | Reduction Alkyl sulfonates Enol triflates Arene catalysis Active copper |
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