8.1.33.4 Transition-Metal-Catalyzed C—C Bond Formation with Organolithium Reagents (Update 2025) DOI
Jaime Mateos, Martín Fañanás‐Mastral

Опубликована: Дек. 13, 2024

Abstract Organolithium compounds are among the most versatile and widely used reagents in organic synthesis. However, their high reactivity basicity have historically limited use as direct coupling partners metal-catalyzed carbon—carbon bond forming methods. This review provides an update to advances this area, with a focus on highlighting reports during period 2011–2023, that revolutionized field, propelling organolithium forefront of strategies for constructing new C—C bonds using transition-metal catalysts.

Язык: Английский

RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution DOI
Jingjing Li,

Jianxun Ye,

Jiayu Zhou

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(31), С. 4905 - 4908

Опубликована: Янв. 1, 2022

The efficient RuPHOX-Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution has been achieved for the synthesis chiral tetrahydronaphthols. mechanism study indicated that with H2 gas, rather than transfer EtOH solvent as hydrogen source, predominates in reaction pathway.

Язык: Английский

Процитировано

13

Desymmetrization of meso-dibromocycloalkenes by copper-catalyzed asymmetric borylative coupling with alkynes DOI Creative Commons
Irene Sánchez‐Sordo, Andrea Chaves‐Pouso, Jaime Mateos

и другие.

Chem Catalysis, Год журнала: 2023, Номер 3(9), С. 100730 - 100730

Опубликована: Авг. 24, 2023

Язык: Английский

Процитировано

6

Synthesis of functionalized tetrahydropyridazines from hydrazones DOI

Sheng Yu,

Jin‐Tao Yu, Changduo Pan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(38), С. 7753 - 7766

Опубликована: Янв. 1, 2024

The tetrahydropyridazine motif is widely present in plenty of natural products and biologically active molecules. Easily prepared from the condensation carbonyls with hydrazines, hydrazones are versatile synthetic building blocks that frequently used organic synthesis. Hydrazones also utilized synthesis nitrogen-containing molecules, especially heterocycles. presence CN-N unit product makes ideal substrates for derivatives. Here, this review, we summarize recent progress construction variously substituted tetrahydropyridazines different hydrazone derivatives together mechanism discussions.

Язык: Английский

Процитировано

2

Palladium/GF-Phos-catalyzed asymmetric carbenylative amination to access chiral pyrrolidines and piperidines DOI Creative Commons
Yue Sun, Chun Ma, Zhiming Li

и другие.

Chemical Science, Год журнала: 2022, Номер 13(37), С. 11150 - 11155

Опубликована: Янв. 1, 2022

The cross-coupling of

Язык: Английский

Процитировано

10

Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties DOI
Prashant Kumar, Pravesh Kumar, Sugumar Venkataramani

и другие.

ACS Catalysis, Год журнала: 2021, Номер 12(2), С. 963 - 970

Опубликована: Дек. 31, 2021

Palladium-catalyzed allylic alkylation reactions of gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, diacetates behave 1,3-dicationic equivalents undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) produce novel polycyclic chromenes possessing spiro-, tri-, tetrasubstituted carbon centers. The versatility method is demonstrated in synthesis several chromene-based bioactive natural products. Further, interesting photochromic properties classes benzo[f]chromenes also discovered.

Язык: Английский

Процитировано

12

The construction of chiral 3-acyl bicyclolactamsviaa RuPHOX/Pd catalyzed asymmetric allylic substitution cascade of α-carbonylamides DOI
Siqi Dong, Shaofeng Xu,

Yashi Zou

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1731 - 1737

Опубликована: Янв. 1, 2023

A RuPHOX/Pd catalyzed asymmetric allylic substitution cascade of α-carbonylamides with an meso -dicarbonate has been developed, providing chiral 3-acyl bicyclolactams in high yields and up to 99% ee >20 : 1 dr.

Язык: Английский

Процитировано

5

RuPHOX-Ru catalyzed asymmetric Guerbet reaction of secondary alcohols with primary alcohols DOI

Jingli He,

Ruhui Li,

Xuezhen Kou

и другие.

Tetrahedron, Год журнала: 2023, Номер 143, С. 133543 - 133543

Опубликована: Июль 11, 2023

Язык: Английский

Процитировано

4

Regio- and Enantioselective Synthesis of Dihydropyrido[1,2-a]indoles via Catalytic Asymmetric Annulative Allylic Alkylation DOI
Xue Wang,

Hui‐Lin Mao,

Yuheng Yang

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(22), С. 15644 - 15652

Опубликована: Ноя. 2, 2022

A palladium-catalyzed asymmetric annulative allylic alkylation reaction of 2-[(1H-indol-2-yl)methyl]malonates with (E)-but-2-ene-1,4-diyl dicarbonates is described, leading to the regio- and enantioselective synthesis dihydropyrido[1,2-a]indoles a chiral cyclic allyl stereocenter adjacent ring-junction nitrogen atom in moderate good yields. The salient features this protocol include mild conditions, broad substrate scope, compatibility substituents as well high stereoselectivities, providing catalytic entry for fabricating pyridoindole scaffolds.

Язык: Английский

Процитировано

5

Ultrasound-assisted bromination of indazoles at the C3 position with dibromohydantoin DOI Creative Commons

Shengneng Ying,

Xingru Liu,

Tao Guo

и другие.

RSC Advances, Год журнала: 2022, Номер 13(1), С. 581 - 585

Опубликована: Дек. 22, 2022

Bromoaryl compounds have attracted great attention in organic chemistry, especially for the synthesis of pharmaceutical intermediates. Herein, we demonstrated a novel and efficient bromination protocol indazoles via C-H bond cleavage to give site-specific 3-bromide products that could be further employed as synthetic blocks prepare drugs. The reaction used DBDMH bromine source, tolerated wide range indazoles, finished 30 min under mild, ultrasound-assisted conditions. Besides, preliminary mechanistic studies revealed this approach was not radical process.

Язык: Английский

Процитировано

4

RuPHOX‐Ru Catalyzed Asymmetric Cascade Hydrogenation of 3‐Substituted Chromones for the Synthesis of Corresponding Chiral Chromanols DOI
Shaofeng Xu,

Wenqi Xu,

Siqi Dong

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(37)

Опубликована: Май 2, 2024

Abstract An efficient RuPHOX−Ru catalyzed asymmetric cascade hydrogenation of 3‐substituted chromones has been achieved under mild reaction conditions, affording the corresponding chiral chromanols in high yields with excellent enantio‐ and diastereoselectivities (up to 99 % yield, >99 ee >20 : 1 dr). Control reactions deuterium labelling experiments revealed that a dynamic kinetic resolution process occurs during subsequent C=O double bond, which is responsible for performance hydrogenation. The resulting products allow several transformations it was shown protocol provides practical alternative strategy synthesis their derivatives.

Язык: Английский

Процитировано

0