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Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides

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Abstract Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in… Click to show full abstract

Abstract Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. Mechanistic insights suggest that the o-benzenedisulfonimide anion act as an electron transfer agent and promotes a catalytic cycle which does not require the presence of photocatalysts or external oxidants.

Keywords: miyaura coupling; arenediazonium benzenedisulfonimides; catalysed suzuki; gold catalysed; suzuki miyaura

Journal Title: Tetrahedron
Year Published: 2018

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