Simultaneous reduction of nitro- to amino-group in the palladium-catalyzed Suzuki cross-coupling reaction

Synergistic Effects of ppm Levels of Palladium on Natural Clinochlore for Reduction of Nitroarenes

“…Reactions were then studied in the presence of 0.003 mol %o fP d( as Pd(OAc) 2 )a dded to 25 mg of each clay.U nder these conditions, 18 %a nd 45 % yields wereo btained for the reactions containing bentonite and clinochlore, respectively (Table S1, entries 2a nd 3). The effects of other solids were also investigated but afforded 4chloroaniline in poor yields (TableS1, entries [4][5][6][7][8]. Performing the reaction in am ixture of H 2 Oa nd THF,h owever,l ed to an improvement in the reactione fficiency,r aising the yield to 71 %( Table S1, entry 9).…”

“…[3] Traditional methods for the reduction of nitro compounds such as using Fe/HCl (BØchamp reduction)h ave drawbacks including slow reactionr ates, the need for costly steam distillation, and generation of large amounts of waste, as well as not being amenable to the presence of acid-sensitive functional groups. [4] Recently,o wing to concernsa bout atom efficiency, compatibility with industrial applications,a nd eco-friendliness, considerable attention has been paid to the use of catalytic hydrogenation in the presence of transition metals such as Pd, [5] Au, [6] Ru, [7] Pt, [8] Cu, [9] Co, [10] Ni, [11] and Fe, [12] as well as various other methods. [13] Among these metals, palladium-catalyzed hydrogenation of the nitro group has provena ne ffective and widely used method for the formation of amines.…”

Direct One-Pot Synthesis of Primary 4-Amino-2,3-diaryl-quinolines via Suzuki-Miyaura Cross-Coupling of 2-Aryl-4-azido-3-iodoquinolines with Arylboronic Acids

“…However, this possibility was ruled out by the absence of triphenylphosphonium oxide in the reaction mixture or crude product (tlc monitoring or 31 P-NMR), which is the expected by-product of hydrolysis of phosphazene derivatives [ 18 ]. Recourse to literature, revealed a paper describing the results of palladium acetate (Pd(OAc) 2 )-catalyzed Suzuki-Miyaura cross-coupling of nitroaryl halides with arylboronic acids in DMF/H 2 O at 150 °C using K 2 CO 3 as a base in the absence or presence of a ligand (PPh 3 or DABCO) [ 29 ]. The reaction afforded the corresponding biaryl derivatives with simultaneous reduction of nitro- to amino group and the authors attributed the reduction of the nitro group to molecular hydrogen based on literature precedent [ 30 ].…”

“…The reaction afforded the corresponding biaryl derivatives with simultaneous reduction of nitro- to amino group and the authors attributed the reduction of the nitro group to molecular hydrogen based on literature precedent [ 30 ]. However, DMF-water mixture failed to reduce nitrobenzene to aniline at 150 °C [ 29 ]. Moreover, PdCl 2 (PPh 3 ) 2 -PCy 3 catalyzed cross-coupling of 1d with PhB(OH) 2 using 2 M K 2 CO 3 in dioxane also afforded 2a (26%), 3d (11%) and 4d (62%) in sequence.…”

Growth of Au–Pd2Sn Nanorods via Galvanic Replacement and Their Catalytic Performance on Hydrogenation and Sonogashira Coupling Reactions

“…The detection of a mixture of hydrogenated and deuterated reduction products indicated that the solvent provided the required H or D atoms. 52,53 Au-Pd 2 Sn NRs, when the reaction was performed at high dilution. Interestingly, St was produced at higher concentration either by reduction of tolan or by a mechanism involving insertion of PhA into the NR-Ph bond.…”