Enantioselective Propargylic Substitution Reactions via Transition Metal–Allenylidene Complexes as Key Intermediates DOI Creative Commons
Yoshiaki Tanabe, Yoshiaki Nishibayashi

Coordination chemistry research., Год журнала: 2024, Номер unknown, С. 100003 - 100003

Опубликована: Дек. 1, 2024

Язык: Английский

Reaction of acylpropargylic alcohols with 1-pyrrolines: A synthetic and quantum-chemical study DOI
Ludmila A. Oparina, Anton V. Kuzmin, Lyudmila A. Grishchenko

и другие.

Tetrahedron, Год журнала: 2025, Номер 177, С. 134566 - 134566

Опубликована: Фев. 28, 2025

Язык: Английский

Процитировано

0

The 12-Ethynylmonocarba-closo-dodecaborate Anion: A Ligand for Metal Alkynide Complexes (M = Li, Na, Ca, Zn) DOI
Na Zhang, Li Wu, Yujie Jin

и другие.

Inorganic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 8, 2025

We report the first isolation of metal alkynide complexes (2a-d) incorporating lithium, sodium, calcium and zinc based on monocarborane endo/exo-dianionic framework [CB11H11-12-C≡C]2-. These are synthesized via deprotonation terminal alkynes optimized using calcium, hexamethyldisilazide bases to achieve enhanced yields crystal stability. X-ray crystallography NMR spectroscopy reveal unique coordination geometries, including a rare chair-shaped Li4C2O2 unit in 2a, multinuclear units 2b-c, hexagonal Zn3C3 2d. Subsequent nucleophilic reactions with benzophenone afford propargylic alcohols (3) high efficiency, demonstrating their utility selective synthetic routes for complex molecular assembly. This work not only highlights reactivity alkali alkaline-earth metals acetylides but also offers valuable insights into structural characteristics potential applications advanced materials catalytic systems.

Язык: Английский

Процитировано

0

Recent Advances in Radical Transformations of Propargylic Alcohols DOI

Meng Liang,

Haojie Ma, Xian‐Rong Song

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(12), С. 2659 - 2677

Опубликована: Апрель 4, 2024

Abstract Propargylic alcohols are regarded as a class of readily available and versatile synthons in organic synthesis. Due to their unique bifunctional character, the transformation propargylic has been widely utilized powerful strategy for construction various functionalized frameworks over past few decades. Recently, radical attracted considerable attention synthetic chemistry. This review summarizes recent progress alcohols. Based on different mechanisms formation underlying these transformations, this divided into four parts: (1) transition‐metal catalyzed transformation; (2) photo‐induced (3) electro‐induced (4) metal‐free or oxidant‐mediated

Язык: Английский

Процитировано

2

Rh-Catalyzed Carbonylative Cyclization of Propargylic Alcohols with Aryl Boronic Acids DOI

Wenxiang He,

Wei-Feng Zheng, Hui Qian

и другие.

Organic Letters, Год журнала: 2024, Номер 26(29), С. 6279 - 6283

Опубликована: Июль 18, 2024

2(3

Процитировано

2

Stereoselective Construction of Trisubstituted 1,3‐Enynes <i>via</i> Aryl to Vinyl 1,4‐Palladium Migration DOI Open Access
Jie Lin, Juan Ma, Liandi Wang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4509 - 4514

Опубликована: Авг. 2, 2024

Abstract Palladium‐catalyzed stereoselective olefinic C−H alkynylation of gem ‐diarylsubstituted ethylenes with propargylic alcohols was achieved to access diverse unsymmetrical 1,3‐enynes. The regio‐ and stereoselectivities were established through a 1,4‐palladium migration from aryl vinyl in the presence 2‐FC 6 H 4 OH as additive. Mechanistic investigations suggest that cleavage bond might not be involved rate‐determining step catalytic process.

Язык: Английский

Процитировано

2

Crystal Structure of the Monocarborane Magnesium(II) Acetylide and Its Use in the Synthesis of α,β-Unsaturated Ketones DOI
Kang Zhang,

Kang Cao,

Jizeng Sun

и другие.

Inorganic Chemistry, Год журнала: 2024, Номер 63(36), С. 16595 - 16599

Опубликована: Авг. 23, 2024

We report the first crystal structure of heteroleptic Grignard reagent

Язык: Английский

Процитировано

2

Palladium-Catalyzed Alkylation and Dienylation of Propargylic Carbonates with Hydrazones through Carbonyl Umpolung DOI
Xue‐Qiang Chu, Ruofei Cheng, Chao‐Jun Li

и другие.

ACS Catalysis, Год журнала: 2023, Номер 14(1), С. 574 - 584

Опубликована: Дек. 26, 2023

Controlling the reaction selectivity to realize divergent syntheses is a permanent pursuit for chemists. Reported herein chemodivergent palladium-catalyzed method that enables synthesis of structurally valuable internal alkynes and/or terminal 1,3-dienes from readily available propargylic carbonates through carbonyl umpolung. In presence Pd catalyst/P-ligand, propargyl alkylation complements traditional coupling nonstabilized nucleophiles with electrophiles by employing carbonyls as source umpolung alkyl carbanions and surrogates organometallic reagents. dienylation chemistry, use Pd–NHC combination regulated product distribution, thus providing catalytic alternative otherwise inaccessible branched sequence allenylation skeletal isomerization in chemoselective regioselective manner. Additionally, versatile products can be transformed resulting 1,3-dienes, further highlighting broad synthetic potential these discoveries.

Язык: Английский

Процитировано

5

Copper‐Catalyzed Sequential C(sp2)−H/C(sp3)−H Annulation of Indoles with Propargylic Alcohols to Access Hydrobenzo[b]carbazoles DOI

Yi‐Rui Zhang,

Zong‐Wang Qiu,

Z. Fu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1320 - 1324

Опубликована: Фев. 2, 2024

Abstract Herein, we describe a copper‐catalyzed sequential C( sp 2 )−H/C( 3 )−H annulation of indoles with propargylic alcohols for the synthesis diversely functionalized hydrobenzo[ b ]carbazole scaffolds. The reaction involves Friedel‐Crafts addition, 1,5‐H shift, 6π electrocyclization, and dearomatization‐aromatization cascade. Importantly, this is report use 2‐(diarylmethyl)indoles as three‐carbon synthons in (3+3) involving indole functionalization under oxidant‐free conditions.

Язык: Английский

Процитировано

1

Diversity-Oriented Synthesis of Indole-Fused Polycyclic Scaffolds via Rhodium-Catalyzed NH-Indole-Directed C–H Coupling of 2-Phenyl-1H-indoles with Propargylic Alcohol Derivatives DOI

Guijiao Xiang,

Yanqiao Wang,

Leipeng Lu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5589 - 5605

Опубликована: Апрель 5, 2024

Diversity-oriented synthesis strategy for the efficient assembly of indole-fused polycyclic scaffolds via rhodium-catalyzed NH-indole-directed C–H coupling with propargylic alcohol derivatives in a regioselective manner was developed. Five 2-phenyl-1H-indole-embedded core skeletons were synthesized. In particular, three different exo-olefin-containing polycycles realized, which may be manipulated further chemistry.

Язык: Английский

Процитировано

1

Indium Promotes Direct Sulfonamidation of Unactivated Alcohols DOI

Yaoyao Ban,

Yuhan Liu, Shuwei Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6345 - 6352

Опубликована: Апрель 11, 2024

An improved protocol has been developed for the direct sulfonamidation of unactivated alkyl alcohols using In(OTf)3 as a Lewis acid catalyst. Although established methods or Brønsted acids have well-studied functionalization alcohols, their substrate scope mainly focuses on π-activated alcohols. In this reaction, aliphatic were evaluated and afforded desired sulfonamide products with good to excellent yields.

Язык: Английский

Процитировано

1