Gold in organic synthesis. Preparation of symmetrical and unsymmetrical biaryls via carbon-carbon coupling from cis-diarylgold(III) complexes

Abstract

At room temperature, reacting cis-[Au(Ar)(M)Cl] with [PhCH2PPh3]Cl (l:l), with PPh3 plus NaC104*Hz0 (1:2:1), or with PPh3 (1:l) leads to a reductive elimination giving gold (1) complexes [PhCH2PPh3] [AuC12], [ A u ( P P~~)~] C~O , , or [AuCl(PPh3)], respectively, and in high yields, the corresponding biaryls Ar-Ar' [Ar = C6H4N=NPh-2, Ar' = Ar (l), C6H4NO2-2 (2), C6F6 (3); Ar = Ar' = C6H3(N=NC6H4Me-4')-2, Me-5 (4); Ar = C6H4CH2NMez-2, Ar' = P h (E), C6H4N=NPh-2 (61, C6H3(N=NC6H4Me-4')-2, Me-5 (711.

Stable and Tunable Phosphorescent Neutral Cyclometalated Au(III) Diaryl Complexes

“…[39][40][41][42][43] It is therefore of interest to investigate these established classes of complexes as potential photoactive materials.…”

Gold‐Catalyzed Allylation of Aryl Boronic Acids: Accessing Cross‐Coupling Reactivity with Gold

“…8 Nevertheless, we were encouraged by our own recent observations that in contrast, aryl-aryl reductive elimination from Au III is remarkably fast. 9 As such, we hypothesized that a process involving oxidative addition to a gold aryl species followed by sp 2 –sp 3 reductive elimination might prove achievable under the influence of a gold catalyst (Scheme 1B).…”

Oxidative Addition of Carbon–Carbon Bonds to Gold

“…Reductive eliminations of C À C bonds from square-planar complexes are common in organometallic chemistry, but very rare with gold and so far limited to C(aryl) À C(aryl) bond formation. [19][20][21] In conclusion, the oxidative addition of CÀC bonds to gold was disclosed. Bent gold(I) complexes [(DPCb)Au] + readily insert into the four-membered rings of biphenylene and benzocyclobutenone.…”