Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

Wu, Xiao‐Feng; Neumann, Helfried; Beller, Matthias

doi:10.1021/cr300100s

Cited by 1,166 publications

(308 citation statements)

References 470 publications

Supporting

Mentioning

302

Contrasting

Unclassified

Order By: Relevance

“…Although some carbonylative cyclization methods have been reported, 56,[88][89][90] they generally require pressurized CO gas and high temperature, which hampers the implementation of these reactions. Therefore, the development of a simple and practical method for the synthesis of cyclic compounds is highly desired.…”

Section: Carbonylative Cyclizationmentioning

confidence: 99%

Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions

Konishi

2018

Chem. Pharm. Bull.

View full text Add to dashboard Cite

The use of toxic gas surrogates in organic reactions instead of the gas itself contributes to enhancing the safety, practicality, and efficiency of the reactions involved. Our efforts toward the creation of toxic gas surrogates and the development of a series of catalytic reactions using these surrogates are described. Improvements in substrate scope during the hydroesterification of alkenes using formates facilitated by the Ru-imidazole catalyst system provided the opportunity to discover that phenyl formate is a useful carbon monoxide (CO) surrogate for the generation of CO and phenol under weakly basic conditions. This discovery triggered the development of highly reactive but stable CO surrogates and a variety of Pd-catalyzed carbonylative transformations. N-Formylsaccharin facilitated the use of additional nucleophiles in carbonylation reactions that provided access to a variety of carbonyl compounds. Detailed experimental and theoretical mechanistic studies into the generation of CO from phenyl formate suggest that CO generation proceeds via a concerted E2 α-elimination. Furthermore, a known surrogate of sulfur dioxide was applied for the first time to the selective syntheses of cyclic sulfonamides and sulfinamides, confirming that the surrogate operates as an "S O" source. Notably, the reactions described herein are scalable and can be performed without the use of external toxic gases and specialized reaction vessels; they are easy and simple to perform and demonstrate enormous potential for industrial application.

show abstract

Section: Carbonylative Cyclizationmentioning

confidence: 99%

Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions

Konishi

2018

Chem. Pharm. Bull.

View full text Add to dashboard Cite

show abstract

“…Palladium-catalyzed oxidative alkoxycarbonylation of alkynes is a simple and powerful tool for the synthesis of complex heterocyclic compounds from easily available starting reagents [1][2][3][4][5]. Over the years, we have successfully applied this effective methodology to access carbonylated compounds in a one-pot fashion [6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine

Pancrazzi

Motti

Costa

et al. 2017

Molbank

View full text Add to dashboard Cite

Abstract:The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo [d] [1,3] oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclizationmethoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1 H-NMR, 13 C-NMR spectroscopies, MS spectrometry, and elemental analysis. The Z configuration around the double bond was unequivocally established by 2D NOESY experiments.

show abstract

“…In recent years, efficient synthetic approaches to construct organic frameworks containing pyrroles have been developed [25][26][27][28][29][30][31][32][33][34][35]. On the other hand, the transition-metal-catalyzed sp 2 C-H amination reaction is one of the most demanding procedures to form C-N bonds [36,37].…”

Section: Introductionmentioning

confidence: 99%

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Mang

Yang

et al. 2016

Catalysts

View full text Add to dashboard Cite

Abstract:The Pd(TFA) 2 -catalyzed [4+1] annulation of chained or cyclic α-alkenyl-dicarbonyl compounds and unprotected primary amines for "one-pot" synthesis of pyrroles is reported here. Enamination and amino-alkene were involved in this practical and efficient tandem reaction. The annulation products were isolated in moderate to excellent yields with O 2 as the terminal oxidant under mild conditions. In addition, this method was applied to synthesize highly regioselective aminomethylated and di(1H-pyrrol-3-yl)methane products.

show abstract

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

Cited by 1,166 publications

References 470 publications

Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions

Creation of Novel Toxic Gas Surrogates and the Development of Safe and Facile Catalytic Reactions

(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Contact Info

Product

Resources

About