Suzuki–Miyaura cross coupling reactions with Phenoldiazonium salts

Abstract

The Suzuki-Miyaura coupling of phenol diazonium salts and aryl trifluoroborates yields 4-hydroxybiaryls in a protecting group-free synthesis.

Denitrogenative Pd/Cu‐catalyzed Suzuki‐type Cross‐coupling of Aryltrifluoroborates with Arylhydrazine Hydrochlorides in Water under Room Temperature

“…Suzuki–type cross‐coupling with organotrifluoroborates through the cleavage of C–N bond providing another alternative for electrophilic reagents (Scheme , C‐N bond). The arenediazonium salts have been applied as electrophilic partners in Pd‐catalyzed Suzuki‐type coupling with organotrifluoroborates via the release of N 2 under mild conditions for a long time . Schmidt et al reported a Pd‐catalyzed Suzuki‐type deacetylation–diazotation–coupling with acetanilides as formal leaving groups…”

Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionali­zation

“…Firstly, a protecting‐group‐free approach was tested by use of a diazonium salt22 with a free carboxylic acid and phenol functionality. Although this diazonium salt had previously been successfully used by us in Matsuda–Heck22 and Suzuki–Miyaura couplings,23 its reaction with 17 failed completely. Under basic conditions, compound 17 was quantitatively recovered, whereas the fate of the diazonium salt could not be clarified.…”

“…Boronic acids,35,64–68 boronates69,70 and organotrifluoroborates23,25,26,71 have previously been used as cross‐coupling partners in Suzuki–Miyaura reactions with other arenediazonium salts. As a test reaction for the coupling with acetamidobenzenediazonium salts, we investigated the reactions of m ‐ 2a and p ‐ 2a with phenylboronic acid ( 26a′ , Table 3).…”

Desulfonative pd‐catalyzed coupling of aryl trifluoroborates with arylsulfonyl chlorides

“…Apart from the classical and/or modified coupling reactions with aryl halides as the electrophiles via the cleavage of C X bonds (Scheme ), organotrifluoroborate reagents can also couple with arylsulfonates via the cleavage of C O bonds (Scheme ), including the more challenging unactivated arylsulfamates . In addition, organotrifluoroborate reagents also have been applied to couplings with aryl diazonium salts via the cleavage of C N bonds using suitable catalytic reaction systems . In recent years, decarboxylative reactions have attracted a great deal of attention in organic synthesis for the construction of carbon–carbon bonds, as carboxylic acids are common, inexpensive and readily available in great structural diversity.…”