Ternary Catalysis Enabled Three-Component Asymmetric Allylic Alkylation as a Concise Track to Chiral α,α-Disubstituted Ketones DOI
Zhenghui Kang, Wenju Chang, Xue Tian

и другие.

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(49), С. 20818 - 20827

Опубликована: Дек. 6, 2021

Multicomponent reactions that involve interception of onium ylides through Aldol, Mannich, and Michael addition with corresponding bench-stable acceptors have demonstrated broad applications in synthetic chemistry. However, because the high reactivity transient survival these situ generated intermediates, substitution-type process, especially asymmetric catalytic version, remains hitherto unknown. Herein, a three-component allylation α-diazo carbonyl compounds alcohols allyl carbonates is disclosed by employing ternary cooperative catalysis achiral Pd-complex, Rh2(OAc)4, chiral phosphoric acid CPA. This method represents first example allylic alkylation an SN1-type trapping which involves convergent assembly two active Pd-allyl species, enol derived from ylides, providing expeditious access to α,α-disubstituted ketones good yields excellent enantioselectivity. Combined experimental computational studies shed light on mechanism this novel reaction, including critical role Xantphos ligand origin

Язык: Английский

3d Transition Metals for C–H Activation DOI
Parthasarathy Gandeepan, Thomas Müller, Daniel Zell

и другие.

Chemical Reviews, Год журнала: 2018, Номер 119(4), С. 2192 - 2452

Опубликована: Ноя. 27, 2018

C–H activation has surfaced as an increasingly powerful tool for molecular sciences, with notable applications to material crop protection, drug discovery, and pharmaceutical industries, among others. Despite major advances, the vast majority of these functionalizations required precious 4d or 5d transition metal catalysts. Given cost-effective sustainable nature earth-abundant first row metals, development less toxic, inexpensive 3d catalysts gained considerable recent momentum a significantly more environmentally-benign economically-attractive alternative. Herein, we provide comprehensive overview on until summer 2018.

Язык: Английский

Процитировано

1970

Electrochemical strategies for C–H functionalization and C–N bond formation DOI Creative Commons
Markus D. Kärkäs

Chemical Society Reviews, Год журнала: 2018, Номер 47(15), С. 5786 - 5865

Опубликована: Янв. 1, 2018

This review provides an overview of the use electrochemistry as appealing platform for expediting carbon–hydrogen functionalization and carbon–nitrogen bond formation.

Язык: Английский

Процитировано

880

Organic Electrochemistry: Molecular Syntheses with Potential DOI Creative Commons
Cuiju Zhu, Nate W. J. Ang, Tjark H. Meyer

и другие.

ACS Central Science, Год журнала: 2021, Номер 7(3), С. 415 - 431

Опубликована: Март 9, 2021

Efficient and selective molecular syntheses are paramount to

Язык: Английский

Процитировано

590

Enantioselective C−H Activation with Earth‐Abundant 3d Transition Metals DOI
Joachim Loup, Uttam Dhawa, Fabio Pesciaioli

и другие.

Angewandte Chemie International Edition, Год журнала: 2019, Номер 58(37), С. 12803 - 12818

Опубликована: Май 11, 2019

Molecular syntheses largely rely on time- and labour-intensive prefunctionalization strategies. In contrast, C-H activation represents an increasingly powerful approach that avoids lengthy of prefunctionalized substrates, with great potential for drug discovery, the pharmaceutical industry, material sciences, crop protection, among others. The enantioselective functionalization omnipresent bonds has emerged as a transformative tool step- atom-economical generation chiral molecular complexity. However, this rapidly growing research area remains dominated by noble transition metals, prominently featuring toxic palladium, iridium rhodium catalysts. Indeed, despite significant achievements, use inexpensive sustainable 3d metals in asymmetric activations is still clearly its infancy. Herein, we discuss remarkable recent progress transformations via organometallic base up to April 2019.

Язык: Английский

Процитировано

378

Catalytic Transformations of Functionalized Cyclic Organic Carbonates DOI
Wusheng Guo, José Enrique Gómez, Àlex Cristòfol

и другие.

Angewandte Chemie International Edition, Год журнала: 2018, Номер 57(42), С. 13735 - 13747

Опубликована: Июнь 6, 2018

Functionalized cyclic organic carbonates and related heterocycles have emerged as highly versatile heterocyclic substrates for ring-opening decarboxylative catalytic transformations allowing the development of new stereo- enantioselective C-N, C-O, C-C, C-S C-B bond formation reactions. Transition-metal-mediated conversions only recently been rejuvenated powerful approaches towards preparation more complex molecules. This minireview will highlight potential structurally with a focus on their synthetic value mechanistic manifolds that are involved upon conversion.

Язык: Английский

Процитировано

324

Synergistic Dual Transition Metal Catalysis DOI

U. Bin Kim,

Da Jung Jung,

Hyun Ji Jeon

и другие.

Chemical Reviews, Год журнала: 2020, Номер 120(24), С. 13382 - 13433

Опубликована: Ноя. 29, 2020

Synergistic catalysis, a type of plural catalysis which utilizes at least two different catalysts to enable reaction between separately activated substrates, has unlocked plethora previously unattainable transformations and novel chemical reactivity. Despite the appreciable utility synergistic specific examples involving transition metals have been limited, as ensuring judicious choice parameters prevent deactivation catalysts, undesirable monocatalytic event(s) leading side products, or premature termination other potentially troublesome outcomes present formidable challenge. Excluding those driven by photocatalytic mechanisms, this review will highlight reported reactions that make use simultaneous catalytic cycles metal catalysts.

Язык: Английский

Процитировано

298

Enantioselective Cobalt(III)‐Catalyzed C−H Activation Enabled by Chiral Carboxylic Acid Cooperation DOI
Fabio Pesciaioli, Uttam Dhawa, João C. A. Oliveira

и другие.

Angewandte Chemie International Edition, Год журнала: 2018, Номер 57(47), С. 15425 - 15429

Опубликована: Окт. 6, 2018

The enantioselective cobalt(III)-catalyzed C-H alkylation was achieved through the design of a novel chiral acid. activation characterized by high position-, regio- and enantio-control under exceedingly mild reaction conditions. Thereby, robust cooperative cobalt(III) catalysis proved tolerant valuable electrophilic functional groups, including hydroxyl, bromo, iodo substituents. Mechanistic studies revealed considerable additive effect on kinetics negative non-linear-effect.

Язык: Английский

Процитировано

200

Resource Economy by Metallaelectrocatalysis: Merging Electrochemistry and C H Activation DOI Open Access
Tjark H. Meyer, Lars H. Finger, Parthasarathy Gandeepan

и другие.

Trends in Chemistry, Год журнала: 2019, Номер 1(1), С. 63 - 76

Опубликована: Март 8, 2019

Язык: Английский

Процитировано

195

Transition metal-catalyzed alkene isomerization as an enabling technology in tandem, sequential and domino processes DOI Creative Commons
Daniele Fiorito,

Simone Scaringi,

Clément Mazet

и другие.

Chemical Society Reviews, Год журнала: 2020, Номер 50(2), С. 1391 - 1406

Опубликована: Дек. 10, 2020

One-pot reactions based on catalytic isomerization of alkenes not only offer the inherent advantages atom-, step- and redox-economy but also enable preparation value-added products that would be difficult to access by conventional methods.

Язык: Английский

Процитировано

175

Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles DOI
Yongchao Wang, Angel A. Cobo, Annaliese K. Franz

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(15), С. 4315 - 4348

Опубликована: Янв. 1, 2021

Catalytic asymmetric MCCRs for enantioselective synthesis of spirooxindoles by using chiral phosphoric acids, amines, bifunctional thiourea/squaramides and metal-based reagents as catalysts.

Язык: Английский

Процитировано

172