Controlled generation of ortho-quinone methides and (4+3) cyclization with 2-indolylalcohols by dual photoredox/Brønsted acid relay catalysis DOI Creative Commons
Dong Liang, Panpan Gao, Zhihan Zhang

и другие.

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Given the significance of oxacyclic frameworks in molecular scaffolds and drug discovery, it is intriguing to precisely construct manipulate such ring systems chemical research. In this area, intermolecular, multicomponent cyclization for synthesis diversely substituted seven-membered oxacycles under simple conditions still a challenge. Here, we report dual photoredox/Brønsted acid relay catalytic strategy situ generation ortho-quinone methides subsequent (4+3) with 2-indolylalcohols. one-pot reaction, two C-C one C-O bonds are formed, providing de novo access various biologically important indole-fused, oxygen-containing heterocycles. By virtue chiral phosphoric acid, an asymmetric version can also be achieved good excellent levels enantioselectivity (up 96:4 er).

Язык: Английский

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications DOI
Mingzhu Lu, Jeffrey Goh, Manikantha Maraswami

и другие.

Chemical Reviews, Год журнала: 2022, Номер 122(24), С. 17479 - 17646

Опубликована: Окт. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Язык: Английский

Процитировано

155

Electrochemical Late-Stage Functionalization DOI Creative Commons
Yulei Wang, Suman Dana, Hao Long

и другие.

Chemical Reviews, Год журнала: 2023, Номер 123(19), С. 11269 - 11335

Опубликована: Сен. 26, 2023

Late-stage functionalization (LSF) constitutes a powerful strategy for the assembly or diversification of novel molecular entities with improved physicochemical biological activities. LSF can thus greatly accelerate development medicinally relevant compounds, crop protecting agents, and functional materials. Electrochemical synthesis has emerged as an environmentally friendly platform transformation organic compounds. Over past decade, electrochemical late-stage (eLSF) gained major momentum, which is summarized herein up to February 2023.

Язык: Английский

Процитировано

148

Electrooxidative Rhodium‐Catalyzed [5+2] Annulations via C−H/O−H Activations DOI Creative Commons
Yulei Wang, João C. A. Oliveira, Zhipeng Lin

и другие.

Angewandte Chemie International Edition, Год журнала: 2021, Номер 60(12), С. 6419 - 6424

Опубликована: Янв. 20, 2021

Abstract Electrooxidative annulations involving mild transition metal‐catalyzed C−H activation have emerged as a transformative strategy for the rapid construction of five‐ and six‐membered heterocycles. In contrast, we herein describe first electrochemical [5+2] cycloadditions to assemble valuable seven‐membered benzoxepine skeletons by C−H/O−H activation. The efficient alkyne annulation featured ample substrate scope, using electricity only oxidant. Mechanistic studies provided strong support rhodium(III/I) regime, benzoxepine‐coordinated rhodium(I) sandwich complex catalyst resting state, which was re‐oxidized rhodium(III) anodic oxidation.

Язык: Английский

Процитировано

75

Electrolytic C–H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis DOI
Seongho Jin, Jinwoo Kim, Dongwook Kim

и другие.

ACS Catalysis, Год журнала: 2021, Номер 11(11), С. 6590 - 6595

Опубликована: Май 20, 2021

Herein, we describe the development of a Rh-catalyzed C–H acyloxylation under mild electrolytic conditions. Anodic oxidation key rhodacyclic carboxylate intermediate was found to enable product-releasing C–O bond-forming reductive elimination process. An accumulation near electrode surface rationalized further induce desired bond formation, allowing an ambient catalytic oxygenation using stoichiometric amounts readily accessible carboxylic acid coupling partners.

Язык: Английский

Процитировано

45

Distal Ruthenaelectro‐Catalyzed meta‐C−H Bromination with Aqueous HBr DOI
Yulei Wang, Hendrik Simon, Xinran Chen

и другие.

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(20)

Опубликована: Фев. 16, 2022

While electrochemical ortho-selective C-H activations are well established, distal continue to be underdeveloped. In contrast, we herein describe the meta-C-H functionalization. The remote bromination was accomplished in an undivided cell by RuCl

Язык: Английский

Процитировано

34

Scalable selective electrochemical oxidation of sulfides to sulfoxides DOI

Zihao Fu,

Haodong Tian,

Shao‐Fei Ni

и другие.

Green Chemistry, Год журнала: 2022, Номер 24(12), С. 4772 - 4777

Опубликована: Янв. 1, 2022

An electrochemical protocol for the selective oxidation of sulfides to sulfoxides has been developed in which NaCl plays a dual role: (1) as an electrolyte transformations and (2) redox mediator avoid sensitive functional groups.

Язык: Английский

Процитировано

30

Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles DOI Creative Commons
Samina Aslam, Najoua Sbei, Sadia Rani

и другие.

ACS Omega, Год журнала: 2023, Номер 8(7), С. 6175 - 6217

Опубликована: Фев. 1, 2023

Numerous applications in the realm of biological exploration and drug synthesis can be found heterocyclic chemistry, which is a vast subject. Many efforts have been developed to further improve reaction conditions access this interesting family prevent employing hazardous ingredients. In instance, it has stated that green environmentally friendly manufacturing methodologies introduced create N-, S-, O-heterocycles. It appears one most promising methods these types compounds avoiding use stoichiometric amounts oxidizing/reducing species or precious metal catalysts, only catalytic are sufficient, represent an ideal way contributing toward resource economy. Thus, renewable electricity provides clean electrons (oxidant/reductant) initiate cascade via producing reactive intermediates facilitate building new bonds for valuable chemical transformations. Moreover, electrochemical activation using metals as mediators identified more efficient strategy selective functionalization. indirect electrolysis makes potential range practical, less side reactions occur. The latest developments electrolytic O-heterocycles main topic mini review, was documented over last five years.

Язык: Английский

Процитировано

18

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs) DOI Creative Commons
Yulei Wang,

Rong Zhao,

Lutz Ackermann

и другие.

Advanced Materials, Год журнала: 2023, Номер 35(49)

Опубликована: Март 25, 2023

Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient atom-economic tools to prepare PAHs under exceedingly mild conditions constitutes a long-term goal. Traditional syntheses largely relied on multistep approaches or the conventional Scholl reaction. However, reactions are inefficient with electron-deficient substrates, require stoichiometric chemical oxidants, typically occur presence strong acid. In sharp contrast, electrochemistry has gained considerable momentum during past decade an alternative for facile straightforward assembly, generally via electro-oxidative dehydrogenative annulation, releasing molecular hydrogen sole byproduct by evolution This review provides overview recent significant advances field electrochemical various until January 2023.

Язык: Английский

Процитировано

18

Modern photo- and electrochemical approaches to aryl radical generation DOI Creative Commons

Krzysztof Grudzień,

Andrei Zlobin,

Jan Zadworny

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(18), С. 5232 - 5277

Опубликована: Янв. 1, 2024

This review describes recent advances in the generation of aryl radicals using light and electricity. Such modern techniques allow for efficient energy resource utilization, thus providing more sustainable radical arylation methods.

Язык: Английский

Процитировано

8

Electrochemical assembly of isoxazoles via a four-component domino reaction DOI Creative Commons
Yuanyuan Zhao, Xinyue Li, Simon L. Homölle

и другие.

Chemical Science, Год журнала: 2023, Номер 15(3), С. 1117 - 1122

Опубликована: Дек. 11, 2023

Multicomponent domino reactions

Язык: Английский

Процитировано

14