Palladium-catalyzed substitution of allylic alcohols with sulfinate salts: A synthesis of bicalutamide. (8th June 2021)

• Record Type: Journal Article
• Authors: Jhang, Yin-Jia; Chang, Chieh-Yu; Lin, Yu-Huan; Lee, Chein-Chung; Wu, Yen-Ku
• Is Part Of: Tetrahedron letters. Volume 73(2021)
• Publication Date: 2021-06-08
• Subjects: Allylation -- CS bond -- Allyl Sulfone -- Palladium Catalysis -- Titanium tetraisopropoxide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: In situ activation of allyl alcohols with Ti(IV) alkoxide and palladium catalysis. Phenylboronic acid displays a favorable additive effect in the title reaction. A concise, four-step conversion of methallyl alcohol to bicalutamide is described. Abstract: A method is presented for the direct substitution of allylic alcohols with sodium arylsulfinates. The process involves a cooperative action of palladium catalysts, phenylboronic acid and titanium tetraisopropoxide. By taking advantage of this protocol, we achieved a concise synthesis of bicalutamide, an anti-androgen compound for treating prostate cancer.