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4.4.33.16 Method 16: Use as Fluorous Labels for Fluorous Synthesis

DOI: 10.1055/sos-SD-004-00740

Keay, B. A.Science of Synthesis, (20024708.

Arylsilanes have been used as fluorous labels for performing fluorous syntheses.[‌181‌‌183‌] The main advantages for using an arylsilane are the ease with which the arylsilicon bond can be cleaved and that three heavily fluorinated alkyl chains can be attached to the silicon atom. For example, a fluorous arylsilane benzyl protecting group 111 has been developed for alcohols and used in the fluorous synthesis of a disaccharide (Scheme 24).[‌184‌] In addition, fluorous arylsilanes 112 (R1=OH) and 112 (R1=Br)[‌185‌] have been used in an Ugi[‌186‌] and Biginelli[‌187‌] reaction, respectively. The arylsilicon bond in the products from the Ugi and Biginelli reactions is cleaved using tetrabutylammonium fluoride in tetrahydrofuran. Surprisingly, the arylsilicon bond was stable to lithium hydroxide in a tetrahydrofuran/water mixture, hydrogen fluoride in pyridine, cesium fluoride in tetrahydrofuran, and trifluoroacetic acid in dichloromethane.

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