Published TCIMAIL newest issue No.197
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Thianthrene for Radical-Mediated Borylation of Alkyl Alcohols
Alkyl thianthrenium salts are generated from alkyl alcohols and thianthrene (1). They are activated by blue light or heat to be converted following a radical pathway into alkyl boronate esters.1) Various alkyl alcohols activated by trifluoromethanesulfonic anhydride react with 1 to afford thianthrenium salts 2. Alkyl radical 3 species induced by blue light (condition A) or heat (condition B) lead to alkyl boronic acid catechol esters 4. Finally pinacol and organic base are added in a one-pot manner, resulting in desired alkyl boronic acid pinacol esters. Alkyl boronic acid pinacol esters are useful synthetic intermediates for various reactions such as cross-coupling reactions, oxidation, amination and halogenation.2)
Related Products
- T0184
- Thianthrene
- T1100
- Trifluoromethanesulfonic Anhydride
- D0691
- Pinacol
- B3757
- Bis(catecholato)diboron
- D3886
- 4,4'-Dimethoxy-2,2'-bipyridyl
- T0424
- Triethylamine
References
- 1) Generation of non-stabilized alkyl radicals from thianthrenium salts for C-B and C-C bond formation
- 2) Stereospecific functionalizations and transformations of secondary and tertiary boronic esters
