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A regio- and stereoselective Heck–Matsuda process for construction of γ-aryl allylsulfonyl fluorides

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A highly efficient regio- and stereoselective Heck–Matsuda method was developed employing aryl diazoniums and allylsulfonyl fluorides for the construction of a class of novel γ-aryl allylsulfonyl fluorides in the presence… Click to show full abstract

A highly efficient regio- and stereoselective Heck–Matsuda method was developed employing aryl diazoniums and allylsulfonyl fluorides for the construction of a class of novel γ-aryl allylsulfonyl fluorides in the presence of Pd(OAc)2 and PPh3. The method features excellent regio- and stereoselectivity (up to 100% E-selectivity), broad substrate scope and mild reaction conditions. Further application of γ-aryl allylsulfonyl fluoride in SuFEx reactions was achieved to provide their corresponding sulfonates and sulfonamides in excellent yields.

Keywords: heck matsuda; aryl allylsulfonyl; allylsulfonyl fluorides; regio stereoselective; stereoselective heck

Journal Title: RSC Advances
Year Published: 2022

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