A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls

Abstract

<p>A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described.</p>

Aryl fluorosulfates: powerful and versatile partners in cross-coupling reactions

“…Recently, in another important development, the same research group demonstrated that phenols 33 can be converted to biaryls 35 in a one-pot process via Suzuki coupling of in situ formed fluorosulfonates with aryl boronic acids 34. 22 The authors identified a combination of Pd(OAc) 2 and Et 3 N as the optimal system for this transformation. As shown in Scheme 10a , the reactions proceed well with both electron-rich and electron-poor partners; however, pyridin-ol derivatives and highly hindered aryl boronic acids ( e.g.…”

New Chemical Transformations Involving SO2F2‐Mediated Alcohol Activation

“…[7] In particular, these aryl fluorosulfonates were employed in a wide range of metal-catalyzed transformations. As a matter of fact, palladium-catalyzed cross-couplings were developed, including Stille, [25] Negishi, [25][26][27] Suzuki, [28][29][30][31][32][33] Heck, [28] Sonogashira [28] and Buchwald-Hartwig [34,35] coupling reactions as well as Pdor Ni-catalyzed cyanation. [36,37] The Ni-catalyzed homocoupling of aryl fluorosulfonates was also reported by Sharpless and co-workers.…”

(Hetero)Aryl Fluorosulfates (ArOSO2F): Good Coupling Partners in Transition‐metal‐catalyzed Reactions

“…The coupling of aryl fluorosulfates with arylboronic acids has advanced throughout the years. In 2020, Yuan et al [81] synthesized 30 biaryl products with different substituents using Pd catalyst under ligandfree conditions. However, this strategy is not applicable to pyridines and natural small molecule substrates.…”