Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source

Gaikwad, Vinayak V.; Mane, Pravin A.; Dey, Sandip; Patel, Divya; Bhanage, Bhalchandra M.

doi:10.1016/j.mcat.2019.110672

Cited by 12 publications

(11 citation statements)

References 64 publications

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“…), at 120°C for 16 h (entry 20). Additionally, the different Pd precursors Pd(OAc) 2 , Pd(dppf)Cl 2 and Ni(dppe)Cl 2 were tested, and the obtained results are shown in Table 1 (entries [22][23][24].…”

Section: Resultsmentioning

confidence: 99%

“…These highly stable, robust complexes showed excellent catalytic activity for Suzuki, [20] Heck, [21] decarboxylative Sonogashira [22] coupling reactions as well as worked for Suzuki, amino, and phenoxy carbonylative coupling reactions. [23] The CÀ C coupling and in-situ reductive cyclization of orthonitro haloarenes and terminal alkynes are more attractive to achieve indole derivative as a one-pot tandem process. The first step involves the Sonogashira coupling reaction, which usually requires Pd catalyst and copper as co-catalyst [24] followed by in situ reductive annulation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

et al. 2022

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An effective process for synthesizing 2-substituted indoles in a one-pot tandem reaction of 1-halo-2-nitrobenzene and terminal alkynes through addition/reductive cyclization is presented. This protocol involves a Sonogashira-type coupling reaction followed by reductive cyclization employing dppf (1,1'bis(diphenylphosphino)ferrocene) ligated Pd dithiolate complex as a catalyst and Zn as an inexpensive reductant. This efficient and tandem process tolerates broad functional groups with moderate to good yields. The gram-scale synthesis of 2substituted indole has also been demonstrated. This protocol provides an alternative route for the synthesis of 2-substituted indoles.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

et al. 2022

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“…[5][6][7] In the last few years, phenoxy carbonylation reactions were reported using aryl halide with phenol in the presence of palladium catalyst using CO gas or solid CO surrogate including Co 2 (CO) 8 , Cr (CO) 6 , and N-formyl saccharine in the presence of palladium catalysts with ligands. [8][9][10] Despite these methodologies being excellent for carbonylative esterification reactions, there are some limitations to the use of expensive palladium catalysts, with additional requirements of moisture-sensitive ligands, co-catalyst, additives, and the handling of CO gas.…”

Section: Introductionmentioning

confidence: 99%

Magnetically separable Ni/Fe₃O₄: An efficient catalyst for phenoxy carbonylation of aryl iodides using bifunctional o‐chlorophenyl formate as a CO source

Mahajan

Kolekar

Bhanage

2023

Applied Organom Chemis

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This work reports the phenoxy carbonylation reactions for the synthesis of aryl esters using magnetically separable nickel supported on Fe3O4. The two main advantages of this process are the use of an inexpensive nickel catalyst and the application of o‐chlorophenyl formate as a both CO source and phenol as a coupling partner. This catalyst is entirely magnetically separable due to the super paramagnetic nature of Fe3O4 and decent reusability potential for up to eight cycles with minimal drops in yields. This protocol tolerates various functionalities of aryl iodides and provided moderate to good yields of corresponding esters. The as‐prepared Ni/Fe3O4 nanoparticles have been characterized using analytical techniques such as FESEM, EDS, TEM, XRD, ICP‐OES, and XPS.

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“…Among various types of such reactions, Pd(II)-catalyzed carbonylation for the synthesis of aromatic esters, such as Pd(OAc) 2 /PPh 3 and PdCl 2 (PhCN) 2 with ferrocenyl phosphine ligands, has been reported . This transformation involves the use of CO gas or solid CO surrogates such as Cr(CO) 6 , Co 2 (CO) 8 , and N -formyl saccharine in the presence of the Pd-ligand catalytic system (Scheme b). − Although the carbonylative esterification reactions occurred efficiently, there are some limitations such as additional requirements of cocatalysts, moisture-sensitive ligands, and additives, especially for reactions involving the use of CO gas that require special precautions because of its highly toxic nature. Additionally, nickel-catalyzed carbonylation of aryl halides with alcohols has also been developed since Bauld reported such reactions under Ni(CO) 4 catalysis .…”

Section: Introductionmentioning

confidence: 99%

Cyclometalated Half-Sandwich Ruthenium Complexes: Preparation, Structure, and Catalytic Synthesis of Phenolic Esters from Aryl Halides without Using External CO under Air

Yang,

Guan,

et al. 2023

Inorg. Chem.

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A series of cyclometalated C,N-chelate halfsandwich ruthenium complexes based on N-heterocyclic ligands were prepared through a simple route with good yields. These airand moisture-stable cyclometalated ruthenium complexes showed excellent catalytic efficiency in phenoxy carbonylation of aryl halides with phenyl formate derivatives as a CO source and phenol as a coupling partner under air. Ester products were obtained with high yields at room temperature and without the need for an inert atmosphere. The excellent catalytic activity, broad substrate range, and mild reaction conditions made this catalytic system potential for industrial production. In addition, DFT study has been carried out to elaborate the possible mechanism of this Ru-catalyzed reaction.

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Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source

Cited by 12 publications

References 64 publications

Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

Magnetically separable Ni/Fe₃O₄: An efficient catalyst for phenoxy carbonylation of aryl iodides using bifunctional o‐chlorophenyl formate as a CO source

Cyclometalated Half-Sandwich Ruthenium Complexes: Preparation, Structure, and Catalytic Synthesis of Phenolic Esters from Aryl Halides without Using External CO under Air

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Supramolecular Pd(II) complex of DPPF and dithiolate: An efficient catalyst for amino and phenoxycarbonylation using Co2(CO)8 as sustainable C1 source

Cited by 12 publications

References 64 publications

Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

Synthesis of 2‐Substituted Indoles by Pd‐Catalyzed Reductive Cyclization of 1‐Halo‐2‐nitrobenzene with Alkynes

Magnetically separable Ni/Fe3O4: An efficient catalyst for phenoxy carbonylation of aryl iodides using bifunctional o‐chlorophenyl formate as a CO source

Cyclometalated Half-Sandwich Ruthenium Complexes: Preparation, Structure, and Catalytic Synthesis of Phenolic Esters from Aryl Halides without Using External CO under Air

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Magnetically separable Ni/Fe₃O₄: An efficient catalyst for phenoxy carbonylation of aryl iodides using bifunctional o‐chlorophenyl formate as a CO source