Desulfonative pd‐catalyzed coupling of aryl trifluoroborates with arylsulfonyl chlorides

Abstract

A Pd‐catalyzed cross‐coupling of aryl trifluoroborates with arylsulfonyl chlorides has been successfully achieved. This transformation is a new method for the Suzuki–Miyaura‐type reaction of aryl trifluoroborates via the cleavage of C S bond, thus providing an alternative synthesis of biaryls. The reported cross‐coupling reactions are tolerant to many common functional groups regardless of electron‐donating or electron‐withdrawing nature, making these transformations attractive alternatives to the traditional Suzuki–Miyaura coupling approaches. Copyright © 2016 John Wiley & Sons, Ltd.

Hetaryl Bromides Bearing the SO2F Group – Versatile Substrates for Palladium‐Catalyzed C–C Coupling Reactions

“…First of all, optimization of the Suzuki reaction conditions was performed using 5-bromopyridine-3-sulfonyl fluoride (10) and phenylboronic acid (36a) as the model compounds (Table 1). [46][47][48] Unfortunately, reaction of hetaryl bromides 10-15 with cyclopropylboronic acid (36d) under the conditions described above was not successful; only starting compounds were recovered. Under these optimized conditions, phenyl (37a-42a), furan-2-yl (37b-42b) and thiophene-2-yl (37c-42c) derivatives of hetaryl sulfonyl fluorides 10-15 were obtained using corresponding aryl boronic acids 36a-c ( It should be noted that all our attempts to prepare thienyl derivatives 38c and 40c from the corresponding aryl bromides 11 and 13 were unfruitful.…”

Chemoselective Reactions of Functionalized Sulfonyl Halides

“…[380] Among them, transition-metalcatalyzed transformations are the most prevalent. In case of functionalized sulfonylchlorides, efficient C(sp 2 )À C(sp 2 ) couplings were reported in the presence of aldehyde, [381] ester, [381][382][383] ketone, [381,[383][384][385][386] phenol, [381] nitro, nitrile, and aryl halogenide [382][383][384][385] functionalities (Scheme 53). Similar conditions that tolerated a ketone moiety were used for the substitution of the SO 2 Cl group with cyanide.…”