624-95-3Relevant articles and documents
Pd-Catalyzed intermolecular C-H bond arylation reactions: Effect of bulkiness of carboxylate ligands
Tanji, Yutaka,Hamaguchi, Ryo,Tsuji, Yasushi,Fujihara, Tetsuaki
supporting information, p. 3843 - 3846 (2020/04/15)
A bulky carboxylic acid bearing one 1-adamantylmethyl and two methyl substituents at the α-position is demonstrated to work as an efficient carboxylate ligand source in Pd-catalyzed intermolecular C(sp2)-H bond arylation reactions. The reactions proceeded smoothly under mild conditions, taking advantage of the steric bulk of the carboxylate ligands.
Reactions of carbene-stabilized borenium cations
Cao, Levy L.,Farrell, Jeffrey M.,Lam, Jolie,Stephan, Douglas. W.
, p. 1839 - 1846 (2020/02/20)
In this paper we probe the reactivity of the borenium cations [C3H2(NCH2C6H4)(NCH2Ph)BH][B(C6F5)4] 2 and [C3H2(NCH2C6H4)2B][B(C6F5)4] 3. The reactions of 2 with cyclohexene or 3,3-dimethyl-1-butene gave the alkyl-aryl borenium salts [PhCH2(CHN)2CCH2C6H4BR][B(C6F5)4] (R = Cy 4, CH2CH2tBu 5) while the corresponding reactions with diphenylacetylene, 1-hexyne and 1-phenyl-1-propyne gave the aryl-alkenyl borenium cation salts [PhCH2(CHN)2CCH2C6H4BC(R1)C(H)R2][B(C6F5)4] (R1 = R2 = Ph 6, R1 = H, R2 = C4H97, R1 = Me, R2 = Ph 8a, R1 = Ph, R2 = Me 8b). In contrast, the reaction of 2 with ethynyldiphenylphosphane or 2-vinylpyridine lead to the formation of the adducts, [PhCH2(CHN)2CCH2C6H4B(H)P(Ph2)CCH][B(C6F5)4] 9, [PhCH2(CHN)2CCH2C6H4B(H)NC5H4C(H)CH2][B(C6F5)4] 10, respectively, while the more bulky donor H2CC(Ph)PMes2 gave 1,2-hydroboration of the phosphinoalkene affording [PhCH2(CHN)2CCH2C6H4BCH2CH(Ph)PMes2][B(C6F5)4] 11. In another vein of reactivity, one or two equivalents of the FLP, PtBu3/B(C6F5)3 is shown to react with 3 to give the zwitterionic borenium-borate species [C2H2(NCH(BC(CHNCH2C6H4)2)C6H4)(NCH(B(C6F5)3)C6H4)CB] 12 and the anionic bis-borate species[tBu3PH][C2H2(NCH(B(C6F5)3)2C6H4)2CB] 13. The implications of these findings are discussed.
Chemoselective continuous-flow hydrogenation of aldehydes catalyzed by platinum nanoparticles dispersed in an amphiphilic resin
Osako, Takao,Torii, Kaoru,Hirata, Shuichi,Uozumi, Yasuhiro
, p. 7371 - 7377 (2017/11/09)
A chemoselective continuous-flow hydrogenation of aldehydes catalyzed by a dispersion of platinum nanoparticles in an amphiphilic polymer (ARP-Pt) has been developed. Aromatic and aliphatic aldehydes bearing various reducible functional groups, such as keto, ester, or amide groups, readily underwent flow hydrogenation in aqueous solutions within 22 s in a continuous-flow system containing ARP-Pt to give the corresponding primary benzylic or aliphatic alcohols in ≤99% yield with excellent chemoselectivity. Moreover, the long-term continuous-flow hydrogenation of benzaldehyde for 8 days was realized, and the total turnover number of the catalyst reached 997. The flow hydrogenation system provides an efficient and practical method for the chemoselective hydrogenation of aldehydes bearing reducible functional groups.