Copper-catalyzed chlorination of functionalized arylboronic acids

Organic Letters

Volumn 12, Issue 6, 2010, Pages 1192-1195

  Wu, Hong ^a   Hynes Jr , John ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORINATED HYDROCARBON; COPPER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BORONIC ACIDS; CATALYSIS; COPPER; HYDROCARBONS, CHLORINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77949858787     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/0l9029337     Document Type: Article

References (43)

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38. 4, filtered, and concentrated, in vacuo. Typically, the material obtained was sufficient in purity. Trace impurities could be removed via column chromatography on silica gel using ether/pentane or EtOAc/heptane as an eluent. Solvent alternatives to MeCN have not been thoroughly investigated.
39. The reported yield for the synthesis of 4a from a potassium trifluoroborate is 64%; see ref 4e.
40. Additional control studies testing the reactivity of various boronic acids with NCS alone wer performed on select substrates. The percent conversion by HPLC under identical conditions in the absence of CuCl are as follows: 1b, 60%; 1c, 0%; 1k, 29%; 1m, 0%. In the absence of CuCl, significant impurities were observed during the reaction of 1c with NCS.
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43. 2 in MeCN at 80 °C for 18 h provided >95% conversion to 2a.