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

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 PPh 3 . The method features excellent regio- and stereoselect...

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Bibliographic Details
Published inRSC advances Vol. 12; no. 30; pp. 19402 - 19405
Main Authors Qin, Hao-Yong, Gui, Houying, Zhang, Zai-Wei, Shu, Tao, Qin, Hua-Li
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 29.06.2022
The Royal Society of Chemistry
Subjects
Aromatic compounds
Chemistry
Fluorides
Selectivity
Stereoselectivity
Substrates
Sulfonamides
Sulfonates
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Summary: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 PPh 3 . 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.
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ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra03733e