Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C–H Activation DOI
Chiranjit Sen,

Bhavesh Sarvaiya,

Souvik Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(23), P. 15287 - 15304

Published: Nov. 3, 2020

A room-temperature C–H bond functionalization of benzamides has been developed by merging a photocatalyst with cobalt catalyst for the synthesis isoindolone spirosuccinimides. The reaction proceeds in aerobic conditions and does not require any sacrificial external oxidants such as Ag(I) or Mn(III) salts. Visible light activates photocatalyst, it acts an electron-transfer reagent helps fundamental organometallic steps modulating oxidation state complex. This spirocyclization showed wide substrate scope good functional group tolerance. possible mechanism was proposed from experimental outcome, showing that activation is irreversible rate-determining step.

Language: Английский

Cobalt(II)-Catalyzed C–H Alkylation of N-Heterocycles with 1,4-Dihydropyridines DOI
Prithwish Ghosh, Na Yeon Kwon,

Youjung Byun

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(24), P. 15707 - 15714

Published: Dec. 7, 2022

The rapid incorporation of alkyl and acyl groups into C–H bonds N-heterocycles is in demand for the development lead candidates drug discovery. Herein, we report cobalt(II)-catalyzed alkylation acylation with 1,4-dihydropyridines (DHPs) as alkylating acylating agents. Notably, a combination KBrO3 Co(II) catalyst was successfully employed generation radicals from DHPs. A series heterocycles, including azauracils, quinoxalinones, pyrazinones, pyridones, quinolones, quinazolinones, xanthines, chromones, azine N-oxides, were compatible under developed conditions. applicability protocol challenging contexts highlighted by selective modification well gram-scale synthesis bioactive molecules. Combined mechanistic investigations aided elucidation plausible reaction mechanism.

Language: Английский

Citations

29
Indole Synthesis by Cobalt-Catalyzed Intramolecular Amidation via the Oxidatively Induced Reductive Elimination Pathway DOI
Aleksandrs Cizikovs,

Emils E. Basens,

Paula A. Zagorska

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(3), P. 1690 - 1698

Published: Jan. 17, 2024

C–H bond activation and functionalization using high-valent cobalt catalysis typically involves a Co(III)/Co(I) catalytic cycle. Because of the lack evidence challenges associated with high reactivity instability Co(IV) intermediates, reports on mechanism investigation involving intermediacy are still underexplored. Herein, we report an efficient synthesis indole-2-carboxylic esters via intramolecular amidation α-amidoacrylates experimental computational studies reaction mechanism, which oxidatively induced reductive elimination from species.

Language: Английский

Citations

6
Recent Advances in the Nickel-Catalyzed Alkylation of C-H Bonds DOI Creative Commons
Franc Požgan, Uroš Grošelj, Jurij Svete

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(9), P. 1917 - 1917

Published: April 23, 2024

Functionalization of C-H bonds has emerged as a powerful strategy for converting inert, nonfunctional into their reactive counterparts. A wide range bond functionalization reactions become possible by the catalysis metals, typically from second row transition metals. First-row metals can also catalyze functionalization, and they have merits greater earth-abundance, lower cost better environmental friendliness in comparison to second-row alkylation is particularly important reaction due its chemical significance applications natural product synthesis. This review covers Ni-catalyzed using alkyl halides olefins sources.

Language: Английский

Citations

6
Traceless Bidentate Directing Group Assisted Cobalt-Catalyzed sp2-C–H Activation and [4 + 2]-Annulation Reaction with 1,3-Diynes DOI
Arnab Dey, Chandra M. R. Volla

Organic Letters, Journal Year: 2020, Volume and Issue: 22(19), P. 7480 - 7485

Published: Sept. 16, 2020

An efficient cobalt-catalyzed [4 + 2] annulation of hydrazones and 1,3-diynes has been developed for the synthesis 3-alkynylated isoquinolines engaging 2-aminopyridine as a traceless bidentate directing group. The strategy successfully extended 3,3′-biisoquinoline moieties via both one-pot well sequential approaches. utilization group with an inexpensive earth-abundant cobalt-catalyst under operationally simple reaction conditions makes present transformation more valuable appealing.

Language: Английский

Citations

47
Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C–H Activation DOI
Chiranjit Sen,

Bhavesh Sarvaiya,

Souvik Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(23), P. 15287 - 15304

Published: Nov. 3, 2020

A room-temperature C–H bond functionalization of benzamides has been developed by merging a photocatalyst with cobalt catalyst for the synthesis isoindolone spirosuccinimides. The reaction proceeds in aerobic conditions and does not require any sacrificial external oxidants such as Ag(I) or Mn(III) salts. Visible light activates photocatalyst, it acts an electron-transfer reagent helps fundamental organometallic steps modulating oxidation state complex. This spirocyclization showed wide substrate scope good functional group tolerance. possible mechanism was proposed from experimental outcome, showing that activation is irreversible rate-determining step.

Language: Английский

Citations

45