Rhodium-catalyzed carbonylation of 2-alkynylaniline: Syntheses of 1,3-dihydroindol-2-ones

Hirao, K.; Morii, Noritsugu; Joh, Takashi; Takahashi, Shigetoshi

doi:10.1016/0040-4039(95)01202-s

Cited by 68 publications

(27 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[188] In particular, by introducing a reactive, tethered functional group, fused cycles such as indolones, [189] tricyclic lactones, [190] isocoumarins, [191] benzofuranones, [192] and isochromanones [193] could be synthesized (Scheme 16). …”

Section: The Water-gas Shift Reaction In Organic Synthesismentioning

confidence: 99%

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Ambrosi

Denmark

2016

Angew Chem Int Ed

View full text Add to dashboard Cite

Since its original discovery over a century ago, the water-gas shift reaction (WGSR) has played a crucial role in industrial chemistry, providing a source of H2 to feed fundamental industrial transformations such as the Haber–Bosch synthesis of ammonia. Although the production of hydrogen remains nowadays the major application of the WGSR, the advent of homogeneous catalysis in the 1970s marked the beginning of a synergy between WGSR and organic chemistry. Thus, the reducing power provided by the CO/H2O couple has been exploited in the synthesis of fine chemicals; not only hydrogenation-type reactions, but also catalytic processes that require a reductive step for the turnover of the catalytic cycle. Despite the potential and unique features of the WGSR, its applications in organic synthesis remain largely underdeveloped. The topic will be critically reviewed herein, with the expectation that an increased awareness may stimulate new, creative work in the area.

show abstract

Section: The Water-gas Shift Reaction In Organic Synthesismentioning

confidence: 99%

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Ambrosi

Denmark

2016

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

“…In 1995 Takahashi and coworkers have described the rhodium-catalyzed cyclocarbonylation of 2-alkylaniline 73 to five-membered ring lactam; once again it was possible to control the selectivity towards 74 or 75 acting on the reaction condition (Scheme 48) [58]. More recently, Gabriele and co-workers reported the palladium oxidative carbonylation reactions of 2-ethynylaniline derivatives in methanol and PdI2/KI as the catalytic system under a 4:1 CO/air mixture at 25°C for the synthesis of (E)-3-(methoxycabonyl)methylene-1,3-dihydroindol-2-ones [59].…”

Section: Synthesis Of Five-and Six-membered Lactams Fused To Aromaticmentioning

confidence: 99%

Synthesis of Heterocycles by Transition Metals-Catalyzed Cyclocarbonylation Reactions

Vasapollo

Mele

2006

COC

View full text Add to dashboard Cite

The synthesis of heterocyclic compounds such as lactones, lactams, pyrrolidinones and others can be achieved by cyclocarbonylation reactions catalyzed by transition metal complexes. The combination of palladium salts with certain different ligands turned out to be the most efficient catalyst systems to accomplish such cyclocarbonylation reactions. New synthetic strategies and novel approaches devoted to the preparation of such compounds having different ring size still remain a stimulating area of academic and industrial research.

show abstract

“…36). (34) The selectivity of the reaction depends mainly on the amount of H 2 O and Et 3 N added into the reaction mixture.…”

Section: Equation 35mentioning

confidence: 99%

The Application of Transition Metal Catalysis for Selective Cyclocarbonylation Reactions. Synthesis of Lactones and Lactams

Ali¹,

Alper²

2000

Synlett

100

View full text Add to dashboard Cite

A variety of 5-, 6-, and 7-membered ring lactones and lactams have become available via carbonylative cyclization reactions catalyzed by different transition metal complexes. Palladium and rhodium complexes are the most widely used catalysts for the cyclization reactions. Furanones can be synthesized either by the catalytic intermolecular cyclocarbonylation of iodoarenes with alkynes or alkynols, or by intramolecular cyclocarbonylation of alkynols. g-Butyrolactones are mainly prepared by the intramolecular cyclocarbonylation of allyl alcohol derivatives catalyzed by palladium(0) complexes and 1,4-bis(diphenylphosphino)butane (dppb). The replacement of dppb by a chiral ligand leads to the formation of optically active γ-butyrolactones. Furthermore, 5-, 6-, and 7-membered ring bicyclic and polycyclic lactones and lactams are obtained by the Pd(II) catalyzed intramolecular cyclocarbonylation of 2-allylphenol and 2-allylaniline derivatives in the presence of syngas. The regiochemical control of the reaction depends on the choice of solvent, the nature of the metal and added ligand, and the relative pressures of the gases (CO and H 2 ). Lactones 2.3Synthesis of Five-, Six-, and Seven-Membered Ring bicyclic and polycyclic Lactones 3Catalytic Synthesis of Five-, Six-, and Seven-Membered Rings Lactams 4Conclusion

show abstract

Rhodium-catalyzed carbonylation of 2-alkynylaniline: Syntheses of 1,3-dihydroindol-2-ones

Cited by 68 publications

References 7 publications

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Synthesis of Heterocycles by Transition Metals-Catalyzed Cyclocarbonylation Reactions

The Application of Transition Metal Catalysis for Selective Cyclocarbonylation Reactions. Synthesis of Lactones and Lactams

Contact Info

Product

Resources

About