A safe, scaleable method for the oxidation of carbon-boron bonds with Oxone®

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5817-5819

  Ripin, David H Brown ^a   Cai, Weiling ^a   Brenek, Steven J ^a  

^a PFIZER INC   (United States)

Author keywords

Carbon boron bond; Hydroboration; Organoborane; Oxidation; Oxone

Indexed keywords

ALCOHOL; BORON; CARBON; ORGANOBORON DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS; REPRODUCIBILITY; TEMPERATURE;

EID: 0013420443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00978-3     Document Type: Article

References (16)

1. Pelter, A.; Smith, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 7, p. 593.
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4. Johnson, J. R.; van Campen, M. G. J. Am. Chem. Soc. 1938, 60, 121.
5. (a) Pappo, R. J. Am. Chem. Soc. 1959, 81, 1010;
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8. Matteson, D. S.; Moody, R. J. J. Org. Chem. 1980, 45, 1091.
9. Kabalka, G. W.; Wadgoonkar, P. P.; Shoup, T. M. Tetrahedron Lett. 1989, 30, 5103.
10. 2: Exothermic decomposition from 31 to 100°C liberating 747 J/g of energy. Reaction calorimetry was performed in an Accelerating Rate Calorimeter (ARC™).
11. No chromatography was necessary. A variety of methods were investigated including TMANO, MCPBA, and sodium perborate. These methods all suffered from either safety concerns (TMANO), incomplete reaction (perborate), or side reactions (MCPBA).
12. DSC for 30% aqueous Oxone®: Exothermic decomposition from 56 to 127°C liberating 86 J/g of energy. Reaction calorimetry was performed in a CRC90e™ reaction calorimeter.
13. 4, and concentrated in vacuo. The residue obtained is pure alcohol (19.0 g, 92%).
14. Compounds 2, 4 and 10 were compared to authentic samples purchased from Aldrich. Compounds 6, 8 and 12 were compared to data reported in the literature. Compound (6): J. Am. Chem. Soc. 1989, 111, 6749; compound (8): Tetrahedron 1970, 26, 5519; compound (12): J. Org. Chem. 1982, 47, 4692.
15. Compounds 2, 4 and 10 were compared to authentic samples purchased from Aldrich. Compounds 6, 8 and 12 were compared to data reported in the literature. Compound (6): J. Am. Chem. Soc. 1989, 111, 6749; compound (8): Tetrahedron 1970, 26, 5519; compound (12): J. Org. Chem. 1982, 47, 4692.
16. Compounds 2, 4 and 10 were compared to authentic samples purchased from Aldrich. Compounds 6, 8 and 12 were compared to data reported in the literature. Compound (6): J. Am. Chem. Soc. 1989, 111, 6749; compound (8): Tetrahedron 1970, 26, 5519; compound (12): J. Org. Chem. 1982, 47, 4692.