Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4875-4878

  McLaughlin, Mark ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; BORONIC ACID DERIVATIVE; PALLADIUM; PHOSPHATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

BENZENE DERIVATIVES; BORONIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PHOSPHATES;

EID: 27644599488     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0517271     Document Type: Article

References (26)

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12. For a recent review of alkyl halide cross-couplings, see: Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
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23. Full details of the phosphate preparations may be found in Supporting Information.
24. When this particular reaction mixture was then heated to 90°C, a 97% assay yield was obtained.
25. Electron-deficient arylboronic acids are less nucleophilic and undergo transmetalation at a slower rate than electron-neutral and electron-rich arylboronic acids. Additionally, electron-deficient arylboronic acids are prone to homocoupling. For a report, see: Wong, M. S.; Zhang, X. L. Tetrahedron Lett. 2001, 42, 4087-4089.
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