Synfacts, Journal Year: 2021, Volume and Issue: 17(07), P. 0769 - 0769
Published: June 17, 2021
Key words nickel catalysis - heteroarylation indoles regioselectivity
Language: Английский
Organic Letters, Journal Year: 2022, Volume and Issue: 24(24), P. 4421 - 4426
Published: June 10, 2022
The electrochemical deconstructive functionalization of cycloalkanols with nucleophiles has been studied, which allows to occur exclusively at the β-position ketones. substrate scope includes a wide range as well diverse N, O, C, and P-centered nucleophiles, providing ready access β-functionalized ketones products. Mechanistic studies support generation α,β-unsaturated key intermediates followed by Michael addition nucleophiles.
Language: Английский
Citations
29
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971
Published: Jan. 1, 2023
A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.
Language: Английский
Citations
14
Green Chemistry, Journal Year: 2024, Volume and Issue: 26(8), P. 4733 - 4741
Published: Jan. 1, 2024
Electrochemical dehydroxymethylative functionalization reactions of aliphatic alcohols with diverse nucleophiles are herein reported.
Language: Английский
Citations
6
Science Bulletin, Journal Year: 2024, Volume and Issue: 69(12), P. 1866 - 1874
Published: April 16, 2024
Language: Английский
Citations
6
Green Chemistry, Journal Year: 2021, Volume and Issue: 23(23), P. 9549 - 9553
Published: Jan. 1, 2021
A metal free, visible-light driven C–H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.
Language: Английский
Citations
32
Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1072 - 1081
Published: March 17, 2023
Abstract Being in its infancy, radical cross‐coupling is highly efficient for C−C bond construction, though suffers from selectivity problems and limited reaction types. New methodologies to realize selectively are desired. Herein, an iron catalyzed deconstructive cyanomethylation of unstrained cyclic linear alcohols with acetonitrile has been developed through cross‐coupling. The unprecedented method enables a ring‐opening functionalization cyclohexanols produce α‐cyanomethyl ketones. Notably, the challenging involves twice single cleavage β‐scission alkoxyl intermediates, C( sp 3 )−H transformation via hydrogen atom transfer (HAT) procedures, resulting two carbon species that process form new )−C( ) selectively. α‐arylketo α‐aryl substituted tertiary can also be applied as substrates, leading terminal cyano‐functionalized products, ketone leaving fragment. Mechanistically, procedure generate chlorine in‐situ formed intermediate cycloalkyl hypochlorite was suggested. magnified image
Language: Английский
Citations
9
Organic Letters, Journal Year: 2021, Volume and Issue: 23(24), P. 9520 - 9525
Published: Dec. 1, 2021
Transition-metal-catalyzed activations of carbon-carbons bonds small strained rings have widespread applications in synthetic and medicinal chemistry. However, coupling reactions cyclobutanols involving β-carbon elimination to construct C(sp3)-C(sp3) scarcely been developed. Here, we demonstrate a highly enantioselective Pd-catalyzed intermolecular reaction broad range cyclobutanol derivatives unactivated alkenes, allowing convenient access series chiral benzene-fused cyclic compounds regio-, chemo-, manner.
Language: Английский
Citations
18
The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(21), P. 14685 - 14694
Published: Oct. 7, 2022
Ring opening of cycloalkanols has been employed as a commonly used strategy to prepare diverse distal functionalized ketones. However, most these ketones obtained by this belong monofunctional ketones, while difunctional with more potential application value have rarely reported. Herein, we first reported mild I2-promoted ring-opening selenation cyclopropanol synthesize various In the reaction, hydroxyl (−OH) derived from water and RSe+ diselenide can be introduced into α- β-positions, respectively, delivering β-hydroxy selenylated in good excellent yields.
Language: Английский
Citations
12
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(2), P. 882 - 886
Published: Jan. 4, 2024
In this work, we describe the unexpected 2-fold Csp3–Csp3 bond cleavage suffered by cyclobutanols in presence of a catalytic amount Pd(OAc)2 and promoted bulky biaryl JohnPhos ligand. Overall, sequential strained an unstrained leads to formal [2 + 2]-retrocyclization products, namely, styrene acetophenone derivatives. This procedure might enable use as masked acetyl groups, resisting harsh conditions organic synthesis.
Language: Английский
Citations
2
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(12), P. 2705 - 2709
Published: May 4, 2024
Abstract A regioselective Markovnikov hydroarylation of arylcyclobutene has been developed using Brønsted acid catalysis through a protonation/Friedel‐Crafts sequence. The metal‐free catalytic reaction is operationally simple and feasible compared to previous reports that utilized elaborate specific polyfluorinated reagents, affording variety gem ‐diaryl‐ substituted in good yields. possible mechanism the explored step‐by‐step control experiments. This protocol involving indole ‐diaryl‐substituted cyclobutene scaffolds not only enriches applications catalyzed hydroarylation, but also paves way for more extensive access potential bioactive cyclobutanes structures.
Language: Английский
Citations
2