1965
DOI: 10.1021/jo01013a069
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Cupric Halide Halogenations

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Cited by 95 publications
(44 citation statements)
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“…Acids 2 and 3 a-c were prepared stereoselectively in good yields, using a previously developed direct halogena-tion reaction of propiolic acid derivatives (Scheme 3). [17] Acid 3 d was obtained by following a procedure, based on that described by Castro et al [18] In a similar study, using b-iodoacrylic acid derivatives as substrates, we reported very similar conclusions. [16] The minimum requirements for good performances in this process were at least 0.2 equivalents of CuI, 2 equivalents of K 2 CO 3 , 2 equivalents of terminal alkyne and the acid in a polar solvent, such as DMF or DMSO, with temperatures between 55 and 65 8C.…”
supporting
confidence: 66%
“…Acids 2 and 3 a-c were prepared stereoselectively in good yields, using a previously developed direct halogena-tion reaction of propiolic acid derivatives (Scheme 3). [17] Acid 3 d was obtained by following a procedure, based on that described by Castro et al [18] In a similar study, using b-iodoacrylic acid derivatives as substrates, we reported very similar conclusions. [16] The minimum requirements for good performances in this process were at least 0.2 equivalents of CuI, 2 equivalents of K 2 CO 3 , 2 equivalents of terminal alkyne and the acid in a polar solvent, such as DMF or DMSO, with temperatures between 55 and 65 8C.…”
supporting
confidence: 66%
“…Its dependence on chloride can also be established because chloride in CuCl 2 is very reactive with many carbon-based compounds. This compound is commonly used for the chlorination of carbonyls 18 and aromatics 19 and as a catalyst for carbonyl compound reactions with alkenes 20 . By fixing the position of the carbon-oxygen ( C O) bond on the surface and reducing CuCl 2 in the electrolyte 21 , we can easily generate an additional redox CuCl layer (Fig.…”
mentioning
confidence: 99%
“…Although we have no evidence about the reaction mechanism, the above intramolecular cyclizations can be explained by the disproportionation of CuBr 2 to CuBr and Br 2 in acetonitrile solution. 24 The generated bromine reacted with the alkene function to form the unstable bromonium cation intermediates which were attacked by sterically close phenolic group. Incidentally, this is an unprecedented route to the synthesis of chroman skeleton.…”
Section: Methodsmentioning
confidence: 99%