Reaction of Coordinated Phosphines. III. Reaction of Phenyl Compounds of Typical Groups V and VI Elements with Palladium(II) Salts in the Presence of Olefinic Compounds

Abstract

The reaction of phenyl compounds of typical groups V and VI elements, PhnA and PhnAX2 (n=2, 3; A=P, As, Sb, Bi, S, Se, Te; X=Cl or X2=O), with Pd(II) salts was studied in the presence of olefinic compounds (1-octene and ethyl acrylate) in acetonitrile. The phenyl migration from A to Pd to produce phenylpalladium species, which lead to the phenylation of olefin, was observed for all PhnA and PhnAX2 (except for A=S and Ph3PX2) when Pd(OAc)2 was utilized. The reaction, however, was inhibited or greatly suppressed for the compounds of P and As when PdCl2 was used in place of Pd(OAc)2. The compounds of Sb and Bi readily react with PdCl2. Mechanistic discussion was given in terms of the extent of nucleophilic assistance by acetate ion when Pd(II) attacks the aromatic nucleus electrophilically at the carbon atom bonded to A.

Study of homo- and cross-coupling competition in the reaction of triarylbismuth(V) dicarboxylates with methyl acrylate in the presence of a palladium catalyst

“…Arylation of vinyl epoxides, diol acetonides and diol carbonates has been performed with both triarylbismuth(III) and triarylbismuth(V) dichloride or carbonate [14]. Several types of organobismuth(III) compounds have been tested in Heck-type reactions [15][16][17]. Bismuth ylides have been used to study a homo-and cross-coupling competition [18].…”

A New Palladium-Catalyzed Phenyl-Alkene Bond Formation

“…This transformation is not completely without precedent, as examples of phenyl transfer from phosphorus [ 3 , 4 ], arsenic [ 5 ] and antimony [ 6 ] have all been reported, albeit usually with specially generated pentacoordinated species. However, this process seems to be unique in its chemoselectivity and ease of implementation.…”

“…A procedure published by Kawamura et al . [ 3 ] provides a similar transformation, but under more stringent conditions, with reaction only on terminal alkenes and with very poor yields, and the reactions are accompanied by various rearrangement products. Treatment of cyclohexene under the conditions of Kawamura et al .…”

Copper-Promoted N-Arylation of 8-Acylaminoquinoline Compounds

“…三苯基铋由于其稳定、相对廉价易得等优点, 在有机合成中受到了许多的关注 [12] . 1977 年, Matsuda 课 题组 [13] 用醋酸钯作催化剂, 三苯基铋为芳源, 实现了烯 烃的芳化反应. 在 2017 年, Nagarkar 课题组 [14] 121.7, 125.9, 126.4, 126.9, 127.4, 127.7, 128.8, 129.0, 129.3, 129.4, 129.8, 136.0, 136.7, 141.8, 144.4, 144.6, 150.8, 171.8 4, 121.6, 125.7, 126.4, 126.9, 127.5, 128.1, 128.7, 129.1, 129.3, 129.3, 129.5, 有机化学 研究论文 135.9, 140.0, 142.0, 144.4, 144.9, 150.7, 171.8 1, 112.8, 121.6, 125.7, 126.4, 126.8, 127.5, 128.1, 128.8, 129.2, 129.3, 131.1, 136.0, 142.2, 144.4, 145.1, 150.7, 160.8, 171.3 8, 126.1, 126.4, 126.8, 127.7, 127.8, 128.9, 129.2, 129.3, 129.4, 130.4, 135.8, 136.0, 141.6, 144.2, 144.4, 150.8, 170.7 8, 124.3, 126.2, 126.5, 126.9, 127.9, 128.9, 129.2, 129.3, 129.5, 130.6, 130.7, 136.0, 141.6, 144.2, 144.4, 150.8, 170.8 1, 121.6, 126.3, 126.4, 127.1, 128.1, 128.1, 128.2, 128.5, 129.6, 129.6, 134.1, 136.0, 137.9, 140.8, 143.0, 144.8, 150.6 8, 36.8, 122.0, 126.0, 126.3, 126.7, 126.9, 128.4, 128.7, 128.9, 129.5, 129.9, 136.3, 140.6, 140.8, 141.5, 143.6, 145.0, 151.4, 173.4 20.3, 33.2, 121.8, 126.1, 126.6, 126.9, 127.3, 128.0, 128.7, 128.9, 129.5, 136.1, 141.2, 144.0, 151.2, 178.8 25.5, 122.4, 125.4, 125.8, 127.0, 127.2, 127.3, 127.4, 128.7, 128.8, 128.9, 129.6, 135.8, 137.1, 141.2, 143.7, 144.7, 159.3, 172.0 5, 125.8, 126.4, 126.9, 127.0, 127.4, 128.4, 128.7, 129.0, 129.2, 129.7, 131.2, 134.5, 136.9, 141.7, 142.7, 144.7, 152.8, 171.7 9, 122.5, 123.8, 125.8, 126.0, 126.9, 127.4, 128.7, 129.0, 129.1, 129.4, 129.7, 137.0, 142.2, 144.2, 144.3, 144.8, 150.5, 171.8 5, 121.7, 125.9, 126.7, 127.0, 127.4, 128.8, 129.0, 129.3, 129.8, 131.3, 135.2, 136.4, 136.8, 141.5, 143.0, 144.8, 150.0, 171.7 124.2, 126.4, 126.8, 127.1, 127.5, 127.6, 128.6, 128.9, 129.2, 129.3, 129.7, 135.9, 137.0, 138.7, 142.0, 144.4, 144.6, 150.7, 171.8 1, 121.6, 126.4, 126.8, 127.4, 127.6, 129.0, 129.2, 129.3, 129.5, 129.7, 135.7, 136.0, 136.9, 142.0, 142.2, 144.4, 150.7, 171. …”