Cobalt(II)‐Catalyzed [5+2] C−H Annulation of o‐Arylanilines with Alkynes: An Expedient Route to Dibenzo‐[b,d]azepines DOI
Fei Ling, Zhen Xie, Jiachen Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2019, Номер 361(13), С. 3094 - 3101

Опубликована: Апрель 29, 2019

Abstract The first example of CoCl 2 ‐catalyzed formal [5+2] oxidative annulation o ‐arylanilines with alkynes was developed, giving access to various important imine‐containing dibenzo‐[ b , d ]azepine scaffolds through sequential C−C/C−N bond formation. reaction employs catalytic amount manganese and oxygen as cooxidants, features a broad substrate scope. Preliminary mechanistic studies suggested that C−H activation is involved in the rate‐determining step. Moreover, both internal terminal are well tolerated this transformation. Besides, regioselective migratory insertion observed when using substrates. magnified image

Язык: Английский

Iron- and cobalt-catalyzed C(sp3)–H bond functionalization reactions and their application in organic synthesis DOI
Yungen Liu,

Tingjie You,

Hai‐Xu Wang

и другие.

Chemical Society Reviews, Год журнала: 2020, Номер 49(15), С. 5310 - 5358

Опубликована: Янв. 1, 2020

This review highlights the developments in iron and cobalt catalyzed C(sp3)–H bond functionalization reactions with emphasis on their applications organic synthesis, i.e. natural products pharmaceuticals synthesis and/or modification.

Язык: Английский

Процитировано

164

Weak-Coordination in C–H Bond Functionalizations Catalyzed by 3d Metals DOI
Rajib Mandal,

Bholanath Garai,

Basker Sundararaju

и другие.

ACS Catalysis, Год журнала: 2022, Номер 12(6), С. 3452 - 3506

Опубликована: Март 3, 2022

Transition-metal-catalyzed C–H bond functionalizations have had an enormous influence on organic synthesis in recent times. However, the use of low-abundance 4d and 5d metals is almost inevitable, they are high demand. This will be a cause concern, hence, it important to develop methods based 3d metals, which widely present Earth's crust. In this regard, metal catalysts or their precursors for catalysis, general, functionalizations, particular, has gained significant momentum The major development catalytic with been achieved predominantly strongly coordinating directing groups such as pyridyl, pyrimidinyl, pyrazolyl, 8-amino-quinolinyl groups. Thus, prefunctionalization substrates these necessary, contradicts step- atom-economy activation. commonly available functional aldehyde, ketone, carboxylic acid, amide, hydroxy, N-oxides loosely bind through weak-coordination. These weakly orient activate regioselectively without need preinstalled Although challenging, contemporary topic actively pursued by many researchers Through article, we provide comprehensive overview metal-catalyzed, coordinating, directing-group-enabled reported until March 2021.

Язык: Английский

Процитировано

118

Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes DOI
Andrew Whyte, Alexa Torelli, Bijan Mirabi

и другие.

Journal of the American Chemical Society, Год журнала: 2020, Номер 142(20), С. 9510 - 9517

Опубликована: Апрель 25, 2020

An asymmetric hydroarylative cyclization of enynes involving a C–H bond cleavage is reported. The cobalt-catalyzed cascade generates three new bonds in an atom-economical fashion. products were obtained excellent yields and enantioselectivities as single diastereo- regioisomers. Preliminary mechanistic studies indicate that the reaction shows no intermolecular crossover. This work highlights potential cobalt catalysis functionalization enantioselective domino reactivity.

Язык: Английский

Процитировано

117

Recent advances and prospects in nickel-catalyzed C–H activation DOI
Nissy Ann Harry, Salim Saranya, Sankuviruthiyil M. Ujwaldev

и другие.

Catalysis Science & Technology, Год журнала: 2019, Номер 9(8), С. 1726 - 1743

Опубликована: Янв. 1, 2019

Nickel-catalyzed C–H activation has become a predominant and ubiquitous research area in organic chemistry.

Язык: Английский

Процитировано

91

Transition Metal Promoted Cascade Heterocycle Synthesis through C−H Functionalization DOI

Alessio Baccalini,

Giuseppe Faita,

Giuseppe Zanoni

и другие.

Chemistry - A European Journal, Год журнала: 2020, Номер 26(44), С. 9749 - 9783

Опубликована: Июнь 18, 2020

Sequential, domino and tandem reactions could be defined as a sequence of synthetic transformations that occur one after the other, in same reaction flask. This Review highlights recent advances at overlap two worlds: transition-metal mediated C-H activation trigger cascade reaction, for heterocycles synthesis. To shed some light on this intricate "middle-earth", focus was put mechanism rather than type metal or chronological order reaction. The aim is to separate, then highlight, true initiated by activation, compared other examples functionalization heterocycle syntheses.

Язык: Английский

Процитировано

76

Co(III), Rh(III) & Ir(III)‐Catalyzed Direct C−H Alkylation/Alkenylation/Arylation with Carbene Precursors DOI
Saiprasad Nunewar, Sanjeev Kumar,

Srilakshmi Talakola

и другие.

Chemistry - An Asian Journal, Год журнала: 2021, Номер 16(5), С. 443 - 459

Опубликована: Янв. 15, 2021

Metal carbenes play a pivotal role in transition-metal-catalyzed synthetic transfer reactions. The metal carbene is generated either from diazo compound through facile extrusion of N2 with catalyst or situ other sources like triazoles, pyriodotriazoles, sulfoxonium ylides and iodonium-ylide. On the hand, Co(III), Rh(III) & Ir(III)-catalyzed C-H functionalizations have been well established as key step to enable construction various transformations. Interestingly, recent years, merging these two concepts activation migratory insertion gained much attention, particular group 9 metal-catalyzed arene precursors via insertion. In this review, we summarize advances direct alkylation/alkenylation/arylation also discuss intermediates within catalytic cycles.

Язык: Английский

Процитировано

66

Manganese‐Catalysed Dehydrogenative Coupling – An Overview DOI
K. Rohit,

Sankaran Radhika,

Salim Saranya

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(8), С. 1602 - 1650

Опубликована: Янв. 29, 2020

Abstract Manganese‐catalysed reactions have attracted great attention recently due to the high relative abundance and cheap eco‐friendly behaviour. Applications of manganese catalysis in cross‐dehydrogenative coupling are among hottest areas since 90% contributions very recent. Dehydrogenation alcohols using Mn‐pincer systems is highly explored nowadays for cross‐coupling synthesise a variety products Mn‐catalysed C−H activation, radical applied dehydrogenative couplings various synthons. This review focuses on synthesis synthetically as well biologically important motifs such carbonyl compounds, olefins, nitrogen heterocycles, amines, imines, etc. manganese‐catalysed reactions. magnified image

Язык: Английский

Процитировано

69

Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach DOI
Avijit Mondal, Rahul Sharma,

Debjyoti Pal

и другие.

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(26), С. 3690 - 3720

Опубликована: Июнь 15, 2021

Abstract Development in the area of acceptorless dehydrogenation (AD) and borrowing hydrogen (BH) catalysis emerge as one potential tools for various C−C C‐heteroatom bond forming reactions. Alcohols, which are important lignocellulosic biomass products, act pivotal electrophilic coupling partners such processes interestingly only H 2 or O is eliminated a byproduct. Initially, was developed by use noble metal catalysts. Recently, base metals Mn, Fe, Co, Ni proved to be environmentally benign inexpensive alternatives application AD BH methods. This transition catalyzed approaches also allow access toward plethora structurally heterocyclic molecules via atom economical strategy. Herein, we summarize current rising expansion heterocycles synthesis through hydrogenation

Язык: Английский

Процитировано

56

Enantioselective Cobalt‐Catalyzed Intermolecular Hydroacylation of 1,6‐Enynes DOI
Andrew Whyte, Jonathan Bajohr, Alexa Torelli

и другие.

Angewandte Chemie International Edition, Год журнала: 2020, Номер 59(38), С. 16409 - 16413

Опубликована: Июнь 11, 2020

Abstract We report a cobalt‐catalyzed hydroacylation of 1,6‐enynes with exogenous aldehydes in domino sequence to construct enantioenriched ketones. The products were obtained good yields excellent regio‐, diastereo‐, and enantioselectivity. Furthermore, the chiral served as valuable precursors access complex spirocyclic scaffolds three contiguous stereocenters. asymmetric process exhibited no C−H crossover KIE, thus indicating that bond cleavage was not involved turnover‐limiting step.

Язык: Английский

Процитировано

53

Recent advances in oxidative allylic C–H functionalization via group IX-metal catalysis DOI
Amaan M. Kazerouni, Quincy A. McKoy, Simon B. Blakey

и другие.

Chemical Communications, Год журнала: 2020, Номер 56(87), С. 13287 - 13300

Опубликована: Янв. 1, 2020

Allylic substitution, pioneered by the work of Tsuji and Trost, has been an invaluable tool in synthesis complex molecules for decades. An attractive alternative to allylic substitution is direct functionalization C-H bonds unactivated alkenes, thereby avoiding need prefunctionalization. Significant early advances were made using palladium catalysis. However, Pd-catalyzed reactions are generally limited terminal olefins with stabilized nucleophiles. Insights from Li, Cossy, Tanaka demonstrated utility RhCpx catalysts functionalization. Since these initial reports, a number key intermolecular Co-, Rh-, Ir-catalyzed have reported, offering significant complementarity reactions. Herein, we report summary recent via group IX-metal π-allyl complexes. Mechanism-driven development new highlighted, potential future developments discussed.

Язык: Английский

Процитировано

51