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30.3.3.2.2.1 Catalyzed by Boron-Based Reagents

DOI: 10.1055/sos-SD-130-00179

Leung, M.-k.; Chou, C.-M.; Luh, T.-Y.Science of Synthesis Knowledge Updates, (20182401.

Boron trifluoride is a mild Lewis acid and has been used to promote condensation of ethane-1,2-dithiol and carbonyl compounds to give 1,3-dithiolanes. The reaction usually proceeds in the presence of excess ethane-1,2-dithiol. Many functional groups such as esters, amines, and furans are tolerated. Selected examples are shown in Scheme 9.[‌19‌‌22‌] Silica gel supported boron trifluoride as well as nano silica gel supported boron trifluoride have been developed;[‌23‌] these catalysts are highly efficient, reusable, and eco-friendly. Chemoselective thioacetalization of aldehydes and ketones gives the corresponding 1,3-dithiolanes 19 (Scheme 9).

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