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A regio- and stereoselective Heck–Matsuda process for construction of γ-aryl allylsulfonyl fluorides†
Hao-Yong Qin,Houying Gui,Zai-Wei Zhang,Tao Shu,Hua-Li Qin
RSC Advances Pub Date : 07/04/2022 00:00:00 , DOI:10.1039/D2RA03733E
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.

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