Methylene C(sp3)–H β,β′-Diarylation of Cyclohexanecarbaldehydes Promoted by a Transient Directing Group and Pyridone Ligand DOI
Sahra St John‐Campbell, Andrew J. P. White, James A. Bull

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(5), P. 1807 - 1812

Published: Feb. 17, 2020

A hindered β-amino amide transient directing group effects di-trans-arylation of cyclohexanecarbaldehydes. The N-substituents are shown to affect yield and can enhance the rate arylation compared with α-amino acid. Addition a pyridone ligand further enhanced reactivity. reaction is successful for range aryl iodides, various substituted cyclohexane carboxaldehydes, providing functionalized products from simple feedstocks. mechanism proposed evoking enamine.

Language: Английский

HFIP in Organic Synthesis DOI
Hashim F. Motiwala,

Ahlam M. Armaly,

Jackson G. Cacioppo

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(15), P. 12544 - 12747

Published: July 17, 2022

1,1,1,3,3,3-Hexafluoroisopropanol (HFIP) is a polar, strongly hydrogen bond-donating solvent that has found numerous uses in organic synthesis due to its ability stabilize ionic species, transfer protons, and engage range of other intermolecular interactions. The use this exponentially increased the past decade become choice some areas, such as C–H functionalization chemistry. In review, following brief history HFIP an overview physical properties, literature examples reactions using or additive are presented, emphasizing effect each reaction.

Language: Английский

Citations

315

Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C–H activation DOI Creative Commons
Trisha Bhattacharya, Animesh Ghosh, Debabrata Maiti

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(11), P. 3857 - 3870

Published: Jan. 1, 2021

Among numerous solvents available for chemical transformations, 1,1,1,3,3,3-hexafluoro-2-propanol (popularly known as HFIP) has attracted enough attention of the scientific community in recent years.

Language: Английский

Citations

201

Transition-metal-catalyzed C–H bond alkylation using olefins: recent advances and mechanistic aspects DOI
Debasish Mandal,

Sumali Roychowdhury,

Jyoti Prasad Biswas

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(17), P. 7358 - 7426

Published: Jan. 1, 2022

Transition metal catalysis has contributed immensely to C-C bond formation reactions over the last few decades, and alkylation is no exception. The superiority of such methodologies traditional evident from minimal reaction steps, shorter times, atom economy while also allowing control regio- stereo-selectivity. In particular, hydrocarbonation alkenes grabbed increased attention due its fundamental ability effectively selectively synthesise a wide range industrially pharmaceutically relevant moieties. This review attempts provide scientific viewpoint systematic analysis recent developments in transition-metal-catalyzed various C-H bonds using simple activated olefins. key features mechanistic studies involved these transformations are described briefly.

Language: Английский

Citations

81

Transient imines as ‘next generation’ directing groups for the catalytic functionalisation of C–H bonds in a single operation DOI
Sahra St John‐Campbell, James A. Bull

Organic & Biomolecular Chemistry, Journal Year: 2018, Volume and Issue: 16(25), P. 4582 - 4595

Published: Jan. 1, 2018

C-H functionalisation promises a paradigm shift in synthetic planning. However, the additional steps often required to install and remove directing groups currently detract from efficiency. The strategy of reversible installation group via an imine linkage has recently emerged, with formed hydrolysed situ. Such transient can promote transition metal catalysed unactivated bonds aldehydes, ketones amines. This approach removes usually for covalent use catalytic quantities forming component. review updates rapidly developing field on sp2 sp3 carbon centres, form new C-C C-X bonds. We focus structures as mono or bidentate coordinating various catalysts.

Language: Английский

Citations

131

Role of hexafluoroisopropanol in C–H activation DOI

Soumya Kumar Sinha,

Trisha Bhattacharya, Debabrata Maiti

et al.

Reaction Chemistry & Engineering, Journal Year: 2018, Volume and Issue: 4(2), P. 244 - 253

Published: Oct. 30, 2018

HFIP has developed immense importance in the C–H functionalization methodology. Both reactivity and selectivity have been vastly improved using whose H-bonding to substrate facilitates accelerates activation. This review summarizes chronological development of evolution activation along with important mechanistic details.

Language: Английский

Citations

130

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation DOI

Ramasamy Manoharan,

Masilamani Jeganmohan

Asian Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 8(11), P. 1949 - 1969

Published: March 13, 2019

Abstract Maleimide and succinimide core moieties are present in various natural products pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines γ‐lactams. A transition‐metal‐catalyzed chelation‐assisted functionalization of inert C−H bond with electrophiles or nucleophiles is one the efficient methods to construct chemical bonds a highly atom‐ step‐economical manner. The review describes recent advances reaction involving maleimides by activation methodology. having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N ‐sulfonyl ketimine, carboxylic acids, aldimines, were described. scope, limitation mechanistic investigation alkylation, annulation alkenylation reactions discussed elaborately. This article includes entire report on bond‐forming strategy until end 2018.

Language: Английский

Citations

123

Transient Ligand‐Enabled Transition Metal‐Catalyzed C−H Functionalization DOI
Ben Niu, Ke Yang,

Brianna Lawrence

et al.

ChemSusChem, Journal Year: 2019, Volume and Issue: 12(13), P. 2955 - 2969

Published: April 8, 2019

Transition metal-catalyzed C-H bond functionalization is among the most efficient and powerful strategies in synthetic organic chemistry to derivatize otherwise inert sites of molecules for construction C-C C-heteroatom bonds. However, additional steps are often required install directing groups realize selective substrates. These tedious run counter step-economical nature activation. In contrast, direct substrate by using transient ligands avoids unnecessary pre-functionalization This Minireview provides a short overview major progress made this field at sp2 sp3 carbon centers with different working modes, including covalent, hydrogen, ionic

Language: Английский

Citations

122

Transient directing ligands for selective metal-catalysed C–H activation DOI
Nupur Goswami, Trisha Bhattacharya, Debabrata Maiti

et al.

Nature Reviews Chemistry, Journal Year: 2021, Volume and Issue: 5(9), P. 646 - 659

Published: July 20, 2021

Language: Английский

Citations

100

Rhodium(iii)-catalyzed C–H activation at the C4-position of indole: switchable hydroarylation and oxidative Heck-type reactions of maleimides DOI
Mahadev Sharanappa Sherikar,

Raja Kapanaiah,

Veeranjaneyulu Lanke

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(79), P. 11200 - 11203

Published: Jan. 1, 2018

A Rh(iii)-catalyzed C–H activation of indole at the C4-position leading to novel and switchable functionalization has been reported by employing a weakly co-ordinating COCF3 group as directing group.

Language: Английский

Citations

93

Transition metal-catalyzed coupling of heterocyclic alkenesviaC–H functionalization: recent trends and applications DOI Open Access
Sundaravel Vivek Kumar, Sonbidya Banerjee, Tharmalingam Punniyamurthy

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(12), P. 1527 - 1569

Published: Jan. 1, 2020

Heterocyclic alkenes and their derivatives are an important class of reactive feedstock valuable synthons. This review highlights the transition-metal-catalyzed coupling heterocyclic alkenesviaa C–H functionalization strategy.

Language: Английский

Citations

84