Thioamide‐Directed Cobalt(III)‐Catalyzed Selective Amidation of C(sp³)−H Bonds

Angewandte Chemie International Edition, Год журнала: 2017, Номер 56(52), С. 16550 - 16554

Опубликована: Окт. 28, 2017

A mild, oxidant-free, and selective Cp*CoIII -catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3 )-H bond activation to generate the desired amidated products is reported. The method efficient allows for C-H a wide range functionalized aryl-, heteroaryl-, alkyl-substituted dioxazolones under conditions. observed regioselectivity towards primary supported by computational studies cyclometalation proposed proceed means an external carboxylate-assisted concerted metalation/deprotonation mechanism. reported rare example use directing group other than commonly used pyridine quinolone classes functionalization first exploit thioamides.

Язык: Английский

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Three-Component Ruthenium-Catalyzed Direct Meta-Selective C–H Activation of Arenes: A New Approach to the Alkylarylation of Alkenes

Journal of the American Chemical Society, Год журнала: 2019, Номер 141(35), С. 13914 - 13922

Опубликована: Авг. 8, 2019

Multicomponent reactions are fundamentally different from two-component reactions, as multicomponent can enable the efficient and step-economical construction of complex molecular scaffolds simple precursors. Here, an unprecedented three-component direct C–H addition was achieved in challenging meta-selective fashion. Fluoroalkyl halides a wide range alkenes, including vinylarenes, unactivated internal were employed coupling partners arenes this strategy. The detailed mechanism presented is supported by kinetic isotope studies, radical clock experiments, density functional theory calculations. Moreover, strategy provided access to various fluoride-containing bioactive 1,1-diarylalkanes other synthetically potential products.

Язык: Английский

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Cobalt(III)-Catalyzed Regio- and Stereoselective α-Fluoroalkenylation of Arenes with gem-Difluorostyrenes

Organic Letters, Год журнала: 2016, Номер 18(24), С. 6320 - 6323

Опубликована: Дек. 5, 2016

A cobalt(III)-catalyzed α-fluoroalkenylation of different arenes with readily available gem-difluorostyrenes has been realized under mild and redox-neutral conditions. This reaction occurs via a C–H activation pathway offers step-economical access to various 1,2-diaryl-substituted monofluoroalkenes in excellent Z selectivity moderate yields.

Язык: Английский

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Recent advances using [Cp*Co(CO)I₂] catalysts as a powerful tool for C–H functionalisation

Dalton Transactions, Год журнала: 2017, Номер 46(30), С. 9721 - 9739

Опубликована: Янв. 1, 2017

This perspective highlights recent applications of Cp*Co^III catalysts in C–H functionalisation protocols, exemplifying both terminal couplings and heterocycle formation.

Язык: Английский

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C–H Alkylations of (Hetero)Arenes by Maleimides and Maleate Esters through Cobalt(III) Catalysis

Organic Letters, Год журнала: 2017, Номер 19(12), С. 3315 - 3318

Опубликована: Июнь 7, 2017

Efficient cobalt(III)-catalyzed (hetero)aryl and alkenyl C–H hydroarylations of maleimides maleate esters have been achieved under remarkably mild reaction conditions. Thus, the versatile cobalt(III) catalyst [Cp*CoI2(CO)] showed excellent atom−and step−economy as well high chemo- site-selectivity providing expedient access to pharmacologically useful succinimides with wide functional group tolerance.

Язык: Английский

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Late‐Stage Peptide Diversification through Cobalt‐Catalyzed C−H Activation: Sequential Multicatalysis for Stapled Peptides

Angewandte Chemie International Edition, Год журнала: 2018, Номер 58(6), С. 1684 - 1688

Опубликована: Ноя. 30, 2018

Bioorthogonal late-stage diversification of structurally complex peptides has enormous potential for drug discovery and molecular imaging. In recent years, transition-metal-catalyzed C-H activation emerged as an increasingly viable tool peptide modification. Despite major accomplishments, these strategies largely rely on expensive palladium catalysts. We herein report unprecedented cobalt(III)-catalyzed activation, which enables the direct functionalization peptides, sets stage a multicatalytic activation/alkene metathesis/hydrogenation strategy assembly novel cyclic peptides.

Язык: Английский

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Transition metal-catalyzed C–H bond functionalization in multicomponent reactions: a tool toward molecular diversity

Organic & Biomolecular Chemistry, Год журнала: 2017, Номер 15(43), С. 9031 - 9043

Опубликована: Янв. 1, 2017

Research advances in transition metal-catalyzed multicomponent C–H functionalization reactions over the last decade are summarized.

Язык: Английский

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Cobalt-Catalyzed Enantioselective Hydroarylation of 1,6-Enynes

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

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Cobalt(III)-Catalyzed C–C Coupling of Arenes with 7-Oxabenzonorbornadiene and 2-Vinyloxirane via C–H Activation

Organic Letters, Год журнала: 2016, Номер 18(15), С. 3802 - 3805

Опубликована: Июль 8, 2016

Co(III)-catalyzed mild C–C couplings of arenes with strained rings such as 7-oxabenzonorbornadienes and 2-vinyloxirane have been realized. The transformation is proposed to undergo ortho C–H activation, olefin insertion, subsequent β-oxygen elimination. A broad range synthetically useful functional groups are compatible, thus providing a new entry access diversely 2-functionalized indoles.

Язык: Английский

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Mild Cobalt(III)‐Catalyzed Allylative C−F/C−H Functionalizations at Room Temperature

Chemistry - A European Journal, Год журнала: 2017, Номер 23(50), С. 12145 - 12148

Опубликована: Июль 4, 2017

Sustainable, cobalt-catalyst enabled, synthetically significant C-F/C-H functionalizations were achieved with an ample substrate scope at ambient temperature of 25 °C, thereby delivering perfluoroallylated heteroarenes. Detailed experimental and computational mechanistic studies on the provided strong support for a facile C-F cleavage.

Язык: Английский

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