Carbonylative Cyclization of Biaryl Enones with Aldehydes and Oxamic Acids DOI
Chada Raji Reddy, Dattahari H. Kolgave,

Sana Fatima

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(24), P. 4901 - 4911

Published: Jan. 1, 2024

An oxidative radical-promoted carbonylative cyclization strategy for the synthesis of phenanthren-9-(10

Language: Английский

Organoelectrophotocatalytic Generation of Acyl Radicals from Formamides and Aldehydes: Access to Acylated 3-CF3-2-Oxindoles DOI
Hong He,

Qinhui Wan,

Zhong‐Wei Hou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 7014 - 7019

Published: Sept. 18, 2023

Organoelectrophotocatalytic generation of acyl radicals from formamides and aldehydes to synthesize acylated 3-CF3-2-oxindoles has been developed. This protocol features a monocatalytic system using 9,10-phenanthrenequinone (PQ) both as catalyst hydrogen atom transfer (HAT) reagent, which avoids the use an external HAT metal oxidant. A variety have obtained in satisfactory yields CF3-substituted N-arylacrylamides via tandem radical cyclization.

Language: Английский

Citations

49
Visible-Light-Induced Synthesis of 1,2-Dicarboxyl Compounds from Carbon Dioxide, Carbamoyl-dihydropyridine, and Styrene DOI
Kimberly Benedetti Vega,

André Luiz Carvalho de Oliveira,

Burkhard König

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 860 - 865

Published: Jan. 22, 2024

β-Amidated carboxylic acids, or succinamic acid derivatives, constitute a valuable chemical scaffold with broad applications in pharmaceuticals, agrochemicals, and polymer sciences. Herein, we report redox-neutral multicomponent reaction for the synthesis of derivatives good yields. This protocol involves styrene, CO2 1,4-carbamoyl-dihydropyridine as radical precursors. The method exhibits substrate scope under mild conditions, including late-stage functionalization. Moreover, by employing 13CO2, enables labeled 1,2-dicarboxylic compounds.

Language: Английский

Citations

6
Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids DOI

Pallav Suman,

Kirti Tomar,

Chandra Shekhar Nishad

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1821 - 1833

Published: Jan. 1, 2024

Metal-free synthesis of medicinally important carbamoylated dihydroquinolinones using readily available, cheap and environment-friendly materials with good to excellent yields.

Language: Английский

Citations

6
Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)–N Bond Cleavage DOI
Akira Shiozuka, Di Wu, Kyohei Kawashima

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 5972 - 5977

Published: April 4, 2024

We report carbamoylarylation of alkenes using N-aryl oxamic acid derivatives under visible-light irradiation. Reactions with carbamoyl radicals generated to afford Giese-type products or 3,4-dihydroquinolin-2(1H)-ones via ortho-radical addition an aryl amide moiety have been previously reported. However, this study reveals that the introduction a removable bulky group onto nitrogen atom acids facilitates radical alkenes, resulting in 1,4-aryl migration C(aryl)–N bond cleavage, thus affording arylpropanamides. Various such as acrylic and styrene derivatives, are successfully applied synthesis variety arylpropanamide including 1,4-dicarbonyl amides, forming two C–C bonds.

Language: Английский

Citations

6
Potassium-modified carbon nitride photocatalyzed-aminoacylation of N‑sulfonyl ketimines DOI

Cailing Wu,

Shaojie Wu, Qifei Huang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(2), P. 110250 - 110250

Published: July 17, 2024

Language: Английский

Citations

6
Visible-Light-Driven Transition-Metal-Free Site-Selective Access to Isonicotinamides DOI
Chunhua Ma, Yu Tian, Junyan Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(45), P. 8265 - 8270

Published: Nov. 7, 2022

The greener synthesis of N-substituted isonicotinamides is high importance and remains a significant challenge to the chemistry community. Herein we delineated visible-light-driven, transition-metal-free, external-oxidant-free radical-radical cross-coupling reaction access via consecutive photoinduced electron transfer (ConPET). utility this protocol highlighted through N-terminal modification peptides late-stage drugs.

Language: Английский

Citations

28
Direct decarboxylative Giese amidations: photocatalytic vs. metal- and light-free DOI Creative Commons

David M. Kitcatt,

Katie A. Scott,

Elena Rongione

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(36), P. 9806 - 9813

Published: Jan. 1, 2023

A direct intermolecular decarboxylative Giese amidation reaction from bench stable, non-toxic and environmentally benign oxamic acids has been developed, which allows for easy access to 1,4-difunctionalised compounds are not otherwise readily accessible. Crucially, a more general acceptor substrate scope is now possible, renders the applicable complex substrates such as natural products chiral building blocks. Two different photocatalytic methods (one via oxidative other reductive quenching cycles) one metal- light-free method were developed flexibility provided by conditions proved be crucial enabling scope.

Language: Английский

Citations

15
Visible light mediated iron-catalyzed addition of oxamic acids to imines DOI Creative Commons

Margaux Badufle,

Frédéric Robert, Yannick Landais

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(18), P. 12528 - 12532

Published: Jan. 1, 2024

Oxamic acids where shown to add imines, providing a broad range of α-aminoacid amides in generally good yields.

Language: Английский

Citations

5
Decarboxylative Nickel- and Photoredox-Catalyzed Aminocarbonylation of (Hetero)Aryl Bromides DOI Creative Commons

Valeriia Hutskalova,

Farhan Bou Hamdan,

Christof Sparr

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(14), P. 2768 - 2772

Published: Oct. 5, 2023

An efficient methodology for the photoredox- and nickel-catalyzed aminocarbonylation of (hetero)aryl bromides was developed. The utilization readily available oxamic acids, application a broadly used organic photoredox catalyst (4CzIPN), mild reaction conditions make this transformation an appealing alternative to classical amidation procedures. generation carbamoyl radicals supported by trapping reactions with hydrogen atom transfer in presence D2O, yielding deuterated formamide. generality deuteration protocol confirmed various acids.

Language: Английский

Citations

11
Photochemical radical decarboxylative disulfuration of α-keto acids and oxamic acids DOI
Huangbin Sun,

Xueting Bin,

Qianfang Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(62), P. 8107 - 8110

Published: Jan. 1, 2024

A visible-light-induced directed decarboxylative disulfuration of α-keto acids and oxamic was developed. As a result, series versatile mono acyl disulfide derivatives synthesized under mild sustainable reaction conditions. This protocol has broad substrate scope, good functional-group tolerance, excellent synthetic applications.

Language: Английский

Citations

4