Keyin Ye

Keyin Ye
Fuzhou University · Department of Chemistry

Doctor of Philosophy

About

60
Publications
3,634
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1,819
Citations
Introduction
We are currently working on the transition-metal catalysis as well as eletrosynthesis.
Additional affiliations
September 2009 - July 2014
Chinese Academy of Sciences
Position
  • PhD Student
September 2005 - July 2009
Xiamen University
Position
  • Student
Education
September 2005 - July 2009
Xiamen University
Field of study
  • Chemistry

Publications

Publications (60)
Article
The Friedel-Crafts type alkylation of C2-tethered thiophenes has been reported to be nonregioselective. Taking advantage of the highly regioselective 5-exo-trig spirocyclization of an electrochemically generated amidyl radical, we have unraveled an electrochemical dearomative spirocyclization of N-acyl thiophene-2-sulfonamides. Various nucleophilic...
Article
Full-text available
α-Azidoketones are valuable and versatile building blocks in the synthesis of various bioactive small molecules. Herein, we describe an environmentally friendly and efficient electrochemical vicinal oxyazidation protocol of α-arylvinyl acetates to afford diverse α-azidoketones in good yields without the use of a stoichiometric amount of chemical ox...
Article
Preparation of biologically relevant 3-hydroxyisoindolinones from readily available 2-alkynylbenzamides is an appealing synthetic approach. However, such kinds of compounds preferably undergo O-attacked 5-exo-dig/6-endo-dig cyclizations. Herein, we report an electrochemically generated amidyl radical proceeding via a highly selective N-attacked 5-e...
Article
Sulfoxides are actively engaged as versatile synthetic building blocks, chiral ligands, bioactive molecules, and function materials. However, their oxidative syntheses from thioethers are inevitably impeded by overoxidation, excess oxidants, and the tedious preparation of thioethers. To address these shortcomings, we report herein a highly selectiv...
Article
A cobalt-catalyzed modular [3+2] assembling of unsaturated hydrocarbons and β-dicarbonyls is reported. This protocol features mild reaction conditions and a broad substrate scope, providing facile entries toward diverse multi-functionalized dihydrofuran...
Article
Herein we report a green and sustainable electrochemical oxidative dearomatization of 2-arylthiophenes. The variation of substitution patterns affords easy access toward both the C2/C3 and C2/C5 difunctionalized dearomative products. The...
Article
Sulfoxide is an important structural motif widely found in medicine, materials, chiral catalysis, and many other fields. The development of green and sustainable synthetic methods for their efficient preparation is...
Article
An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This...
Article
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation an...
Preprint
Full-text available
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation an...
Preprint
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation an...
Article
Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. S...
Article
The selective functionalization of o-carboranes is a popular topic in carborane chemistry. o-Carborane has been widely used in aggregation-induced luminescent materials, nonlinear luminescent materials and other function materials due to its special 3D-aromaticity. The π conjugated systems-tethered o-carboranes could further broaden its application...
Article
Full-text available
As one of the most important biogeochemical cycles, the carbon dioxide (CO2) cycle between atmosphere and biosphere has a profound impact on the life on earth. Therefore, the search for sustainable solutions to normalize the currently unbalanced carbon dioxide cycle is the central research topic of many scientific disciplines. The green and sustain...
Article
Electrochemical hydrogenation of unsaturated organic compounds is emerging as a very promising alternative to the conventional transition-metal-catalyzed transformation as it avoids the preparation, transportation, and storage of pressured molecule hydrogen (H2). Besides the direct usage of the on-site generated H2 on the cathode surface, the elect...
Article
The merger of transition-metal catalysis and electrochemistry has been emerging as a very versatile and robust synthetic tool in organic synthesis. Like in their non-electrochemical variants, ligands also play crucial roles in fundamental reactions in transition-metal catalysis under electrochemical conditions. Herein, a perspective on the roles of...
Article
The selective functionalization of carboranes has received increasing research interests due to their wild applications in chemistry, life, and material sciences. Among various structurally diverse carboranes, the development of selective functionalization of the commercially available o-carborane (1,2-C2B10H12) has largely focused on the two acidi...
Article
Full-text available
Unlike many other state-of-the-art transition-metal-catalyzed allylic substitutions, cobalt has received much less attention of synthetic chemists for a long time despite the fact that cobalt is an earth-abundant, low-cost and thus much more sustainable option as being either reagent or catalyst in organic synthesis. Recently, there is an upsurge o...
Article
Full-text available
There is an increasing demand of using the low-cost and sustainable cobalt to replace its noble congeners (rhodium and iridium) as reflected by the recent upsurge of cobalt catalysis in the diverse organic transformations. Since all the redox reactivity of cobalt catalysis highly relies on the capability of the interconversion between their oxidati...
Article
Full-text available
Given the fact that aldehydes are among the most fundamental and versatile building blocks in organic synthesis, the development of highly efficient and selective methods for their preparation, especially for those delicately functionalized ones remains significant challenging. To address such an issue, Xu and co-workers have recently reported an e...
Article
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Recent advances on the investigation of cobalt fluorides in organofluorine chemistry are highlighted. The preparation and reactivity of inorganic as well as organometallic cobalt fluorides are discussed. The in-depth understanding...
Article
Full-text available
A redox neutral radical-relay cobalt-catalyzed intramolecular C-H fluorination of N-fluoroamides featuring the in situ formed cobalt fluorides as the latent radical fluorinating agents is reported. Moreover, the reactivity of such a cobalt catalysis could be diverted from C-H fluorination to amination by engineering substrates' conformational flexi...
Article
Full-text available
The chemists’ pursuit of the ideal synthesis and functionalization of indole derivatives has lasted over 150 years as their scaffolds have been widely found in natural products, pharmaceuticals, agrochemicals and organic materials. In this regard, the recent resurgence of adopting green and sustainable electrochemistry in organic synthesis is a pro...
Article
Full-text available
Photochemistry and electrochemistry are two powerful tools in organic synthesis as reflected by recent resurgence of both research areas. Despite the impressive advances achieved so far, both synthetic technologies suffer from their innate disadvantages. The constructive merger of photochemistry and electrochemistry, therefore, is capable to fill t...
Article
Full-text available
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- an...
Preprint
Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- an...
Article
Full-text available
Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C–C bond formation remains challenging. Herein, we describe the development of a Ti(III)-catalyzed radical addition of 2° and 3° alkyl chlorides to el...
Article
Full-text available
The stereoselective synthesis of chlorotrifluoromethylated pyrrolidines was achieved using anodically coupled electrolysis, an electrochemical process that combines two parallel oxidative events in a convergent and productive manner. The bench‐stable and commercially available solids CF3SO2Na and MgCl2 were used as the functional group sources to g...
Article
The emergence of new catalytic strategies that cleverly adopt concepts and techniques frequently used in areas such as photochemistry and electrochemistry has yielded myriad new organic reactions that would be challenging to achieve using orthodox methods. Herein, we discuss the strategic use of anodically coupled electrolysis, an electrochemical p...
Article
Full-text available
The open, noninteracting vicinal P/B frustrated Lewis pair (FLP) at the very rigid, dibenzobicyclo[2.2.2]octadiene (“semi-triptycene”) framework shows a trans 1,2-arrangement of the Mes2P– and (C6F5)2B– Lewis base/Lewis acid pair. It is an active dihydrogen splitting reagent and shows a great variety of typical frustrated Lewis pair reactions under...
Article
Systematic study on employing the D-camphor derived carbenes as the chiral ligands in iridium-catalyzed intramolecular allylic amination reaction was carried out. Under mild reaction conditions, enantioenriched indolopiperazinones were obtained in good yields (75-95%) and high enantioselectivity (88-94% ee).
Article
Carbon monoxide is reduced by HB(C6F5)2 at the Mes2PCH2CH2B(C6F5)2 P/B FLP template to give the respective FLP stabilized (η(2)-formyl)borane product 2. This adds sulfur dioxide by insertion of a SO bond into the three-membered ring to give the P/B FLP coordinated SO2 adduct 9.
Article
The -phosphanyl ferrocene carbaldehyde (pS)-1 was converted to the -styryl derivative (pS)-4 by Wittig-Horner olefination. Subsequent hydroboration with Piers' borane [HB(C6F5)2], followed by H2-splitting and crystallization gave the phosphonium/hydridoborate product (pS,R)-5, which was used as a FLP catalyst for the asymmetric hydrogenation of a s...
Article
Coupling of carbon monoxide with nitrogen monoxide was achieved at a frustrated Lewis pair template. This unique reaction uses hydride as an auxiliary, which reductively activates carbon monoxide at the frustrated Lewis pair. The CO/NO coupling reaction then takes place through a pathway involving a radical reaction in which the hydrogen atom auxil...
Article
Coupling of carbon monoxide with nitrogen monoxide was achieved at a frustrated Lewis pair template. This unique reaction uses hydride as an auxiliary, which reductively activates carbon monoxide at the frustrated Lewis pair. The CO/NO coupling reaction then takes place through a pathway involving a radical reaction in which the hydrogen atom auxil...
Article
A chiral iridium(I) N-heterocyclic carbene complex was reported for the first time as the catalyst in the highly enantioselective intramolecular allylic amination reaction. The current method provides facile access to biologically important enantioenriched indolopiperazinones and piperazinones in good yields (74-91 %) and excellent enantioselectivi...
Article
A chiral iridium(I) N-heterocyclic carbene complex was reported for the first time as the catalyst in the highly enantioselective intramolecular allylic amination reaction. The current method provides facile access to biologically important enantioenriched indolopiperazinones and piperazinones in good yields (74–91 %) and excellent enantioselectivi...
Article
The methyl labelled C3 -bridged frustrated phosphane borane Lewis pair (P/B FLP) 2 b was prepared by treatment of Mes2 PCl with a methallyl Grignard reagent followed by anti-Markovnikov hydroboration with Piers' borane [HB(C6 F5 )2 )]. The FLP 2 b is inactive toward dihydrogen under typical ambient conditions, in contrast to the C2 - and C4 -bridge...
Chapter
This chapter summarizes the recent achievements in the area of asymmetric functionalization reactions of C-H bonds via a transient carbon-metal (C-M) species (focusing on contributions after 2009). Compared with the traditional cross-coupling reactions, where C-X and C-M bonds are coupled, mediated by transition metal complexes, these reactions emp...
Article
An efficient Ru-catalyzed regioselective allylic trifluoromethylthiolation reaction of allylic carbonates was developed. The linear allylic trifluoromethyl thioethers were obtained in 52-91% yields. Mechanistic investigation revealed that this reaction proceeds via a double allylic trifluoromethylthiolation sequence.
Article
Full-text available
A class of novel, easily accessible and air-stable 1-[bis(trifluoromethyl)phosphine]-1'-oxazolinylferrocene ligands has been synthesized from ferrocene. It became apparent that these ligands can be used in the regio- and enantioselective Pd-catalyzed allylic alkylation of monosubstituted allyl substrates in a highly efficient manner. Excellent regi...
Article
Regio- and enantioselective synthesis of N-allylindoles was realized through an iridium-catalyzed asymmetric allylic amination reaction with 2-alkynylanilines and subsequent transition-metal-catalyzed cyclization reactions. The highly enantioenriched allylic amines prepared from Ir-catalysis were treated with catalytic amount of NaAuCl4×2 H2O or Pd...
Article
β-Lactam scaffolds are considered to be ideal building blocks for the synthesis of nitrogen-containing compounds. A new palladium-catalyzed oxidative carbonylation of N-allylamines for the synthesis of α-methylene-β- lactams is reported. DFT calculations suggest that the formation of β-lactams via a four-membered-ring transition state is favorable....
Article
An air-stable (pi-allyl)iridium complex derived from naphthocyclooctatetraene and a phosphoramidite ligand has been synthesized and found to be highly efficient in iridium-catalyzed allylic substitution reactions. This catalyst features excellent regioselectivity and high stability. When NaCH(CO2Me)(2) was used as the nucleophile, the catalyst load...
Article
A chemo- and regioselective iridium-catalyzed dienylation of ortho-aminostyrene derivatives with dienyl carbonates was realized. With a catalyst generated from [Ir(cod)Cl]2 (2mol%) and a racemic phosphoramidite ligand (4mol%), 1Z,4E,6E-trienes were obtained in moderate to good yields with exclusive formation of a cis double bond. Tri-ing and succee...
Article
Iridium‐catalyzed asymmetric etherifications of allylic carbonates with 2‐vinylphenols and 2‐allylphenols were realized. With a catalyst generated from 2 mol% of [Ir(cod)Cl]2 (cod=cycloocta‐1,5‐diene) and 4 mol% of the phosphoramidite ligand L2, the etherification products were obtained in excellent ees and then subjected to the ring‐closing metath...
Article
Full-text available
Iridium-catalyzed asymmetric allylic amination of allylic carbonates with 2-allylanilines was realized. With a catalyst generated from 2 mol% of [Ir(dbcot)Cl](2) (dbcot = dibenzo[a,e]cyclooctatetraene) and 4 mol% of phosphoramidite ligand (L3), the amination products were obtained in up to 99% yield and 99% ee. Subjecting amination products to trif...
Article
An Ir-catalyzed allylic vinylation reaction of allyl carbonates with o-aminostyrene derivatives has been realized, providing skipped (Z,E)-diene derivatives. With (E)-but-2-ene-1,4-diyl dimethyl dicarbonate as the substrate, an efficient enantioselective synthesis of 1-benzazepine derivatives via an Ir-catalyzed domino allylic vinylation/intramolec...
Article
Spirocyclohexadienone derivatives are obtained in high yields and enantioselectivities by intramolecular asymmetric allylic dearomatization of phenols bearing tethered allylic ethers.
Article
Direct entry: One-pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α-alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (?)-cassine.
Article
(Figure Presented) Be dazzled by the sequence: The first efficient and general one-pot method for the reductive bisalkylation of lactams/ amides with Grignard and organolithium reagents has been developed (see scheme; DTBMP = 2,6-di-tert-butyl-4methylpyridine, Tf=trifluoromethanesulfonyl).

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