B-Alkylcatecholboranes as a Source of Radicals for Efficient Conjugate Additions to Unsaturated Ketones and Aldehydes

✍ Scribed by Cyril Ollivier; Philippe Renaud

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 145 KB
• Volume: 5
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/(sici)1521-3765(19990503)5:5<1468::aid-chem1468>3.0.co;2-7

✦ Synopsis

Selective and efficient generation of alkyl radicals from alkenes as well as their addition to unsaturated ketones and aldehydes is reported. The method is based on a simple one-pot procedure involving the hydroboration of the alkene with catecholborane, followed by treatment with a catalytic amount of oxygen in the presence of DMPU and a radical trap. Examples of cyclization and cascade reactions are reported.