Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions

Anna Roglans, Anna Pla-Quintana, Marcial Moreno-Mañas

Research output: Contribution to journalReview articleResearchpeer-review

627 Citations (Scopus)

Abstract

This review covers all typical palladium-catalyzed cross-coupling reactions in which diazonium salts have been used as electrophilic partners instead of the more usual halides or oxygen-based electrophilic components. Emphasis is on the Matsuda-Heck, Suzuki-Miyaura, carbonylative couplings, Stille, C-heteroatom couplings and miscellaneous reactions. The section on Matsuda-Heck reaction covers olefinic coupling partner, nature of arenediazonium salts, superior reactivity of N2 as the nucleofuge, effect of bases and other additives, improved catalytic systems, application in synthesis, mechanistic studies and related Matsuda-Heck reactions. The section on Suzuki-Miyaura reaction includes early studies, modification of the boronic counterpart, improved catalytic systems, superior reactivity of N2 as the nucleofuge and carbonylative coupling.
Original languageEnglish
Pages (from-to)4622-4643
JournalChemical Reviews
Volume106
Issue number11
DOIs
Publication statusPublished - 1 Nov 2006

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