Ultrasound-Assisted Remote Benzylic C(sp3)–H Alkylation of N-Fluoroamides with Enol Silanes DOI
Boyi Wang, Tianyu Lu, Ziyu Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16473 - 16484

Опубликована: Ноя. 7, 2024

We have developed an ultrasound-assisted remote benzylic C(sp3)–H alkylation of N-fluorobenzamides with enol silanes; a series β-aryl substituted propiophenones was generated in good to high yields. This reaction represents formal C(sp3)–C(sp3) coupling and features simplicity, efficiency, wide substrate scope multiple-step sequential process, which involves N–F homolysis, 1,5-hydrogen atom transfer, radical addition, oxidation by copper(II) salt, removal the trimethylsilyl group. Also, DFT theoretical calculations Marcus theory were employed consolidate proposed mechanism.

Язык: Английский

Nickel-Catalyzed Modular Four-Component 1,4-Alkylcarbonylation of 1,3-Enynes to Tetra-Substituted CF3–Allenyl Ketones DOI

Qi-Chao Shan,

Yan Zhao, Shutao Wang

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(4), С. 2144 - 2150

Опубликована: Янв. 25, 2024

The modular four-component carbonylation of unsaturated hydrocarbons represents an elegant strategy for the one-pot synthesis complex carbonyl compounds. However, this is currently focused on 1,2-difunctionalization olefins or alkynes, and 1,4-alkylcarbonylation 1,3-enynes remains unexplored. In study, we report a Ni-catalyzed CF3-containing under 1 atm CO, which affords tetra-substituted CF3-allenyl ketones with good yields selectivity. This protocol features mild conditions, broad substrate scope, acceptable functional group compatibility. Control experiments revealed that reactivity oxime esters (regulated by leaving groups) polarity matching are crucial success cascade. Preliminary mechanistic studies suggest acyl nickel key intermediate in transformation.

Язык: Английский

Процитировано

27

Nickel-Catalyzed Carbonylative Negishi Cross-Coupling of Unactivated Secondary Alkyl Electrophiles with 1 atm CO Gas DOI

Yetong Zhang,

Qihang Cao,

Yang Xi

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(12), С. 7971 - 7978

Опубликована: Март 14, 2024

We describe a nickel-catalyzed carbonylative cross-coupling of unactivated secondary alkyl electrophiles with the organozinc reagent at atmospheric CO gas, thus allowing expedient construction unsymmetric dialkyl ketones broad functional group tolerance. The leverage newly developed

Язык: Английский

Процитировано

17

Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives DOI
Ming Li,

Shan-Mei Xu,

Dong‐Ping Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7741 - 7746

Опубликована: Май 14, 2024

A novel three-component cyclization carbonylation reaction of iodoarene-tethered propargyl ethers with amine and CO is reported. This palladium-catalyzed cascade undergoes a sequence oxidative addition, unsaturated bond migration, carbonyl insertion, nucleophilic attack to deliver the benzofuran skeleton. Both aromatic amines aliphatic could proceed smoothly in this transformation under one atm CO.

Язык: Английский

Процитировано

6

Cu-catalyzed alkylarylation of alkenes via N-directed remote C(sp3)–H functionalization DOI
Rong Rui, Bin Wang,

Xiaojing Xu

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1484 - 1489

Опубликована: Янв. 1, 2024

Herein, we report a copper-catalyzed alkylarylation reaction of alkenes using N -fluoroamides and arylboronic acids.

Язык: Английский

Процитировано

4

Nickel-Catalyzed Narasaka–Heck Cyclization Carbonylation of Unsaturated Oxime Esters with Arylboronic Acids DOI
Ming Li,

Fan Gao,

Shan-Mei Xu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7834 - 7840

Опубликована: Сен. 5, 2024

The Narasaka-Heck reaction is one of the most straightforward methods for constructing pyrroline derivatives. Herein, we report a novel nickel-catalyzed three-component carbonylation reaction, which cleverly realizes continuous construction C(sp

Язык: Английский

Процитировано

4

Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones DOI

Hucheng Ma,

Chen-Yang Hou,

Ruyi Zhao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of N-allylbromoacetamides toward the synthesis 2-pyrrolidinone derivatives has been developed with arylboronic acids as reaction partner. This proceeds through a sequential single-electron-transfer pathway via 5-exo-trig cyclization carbonyl insertion steps, furnishing variety in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied CO source here nickel catalyst, which provides supplement for carbonylation chemistry heterocycle synthesis.

Язык: Английский

Процитировано

0

Palladium-Catalyzed and Photoinduced Site-Selective Alkynylation and Oxidation of the Remote C(sp3)–H DOI
Panpan Li,

Zhi Yang,

Shao-Qun Cai

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 10, 2025

A general and efficient method for the direct alkynylation oxidation of remote C(sp3)-H bonds under photoirradiation is described. In this reaction, Pd catalyst acts as both a photocatalyst to generate nitrogen radical cross-coupling with terminal alkyne. Attractive features system include good functional group tolerance, scalability, convenient reagents, an operating system. The utility protocol highlighted by its application derivatization several valuable aza-heterocycles such caspase-3 inhibitor azepinone derivatives.

Язык: Английский

Процитировано

0

Nickel/Photoredox-Catalyzed Carbonylative Cross-Electrophile Coupling of Organohalides and Carboxylic Acid Esters with Phenyl Formate DOI
Xiao‐Biao Yan,

Ning Wang,

Jining Zhou

и другие.

Organic Letters, Год журнала: 2024, Номер 26(30), С. 6518 - 6522

Опубликована: Июль 22, 2024

A photoinduced nickel-catalyzed reductive carbonylative coupling from organohalides and

Язык: Английский

Процитировано

1

Ultrasound-Assisted Remote Benzylic C(sp3)–H Alkylation of N-Fluoroamides with Enol Silanes DOI
Boyi Wang, Tianyu Lu, Ziyu Wang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16473 - 16484

Опубликована: Ноя. 7, 2024

We have developed an ultrasound-assisted remote benzylic C(sp3)–H alkylation of N-fluorobenzamides with enol silanes; a series β-aryl substituted propiophenones was generated in good to high yields. This reaction represents formal C(sp3)–C(sp3) coupling and features simplicity, efficiency, wide substrate scope multiple-step sequential process, which involves N–F homolysis, 1,5-hydrogen atom transfer, radical addition, oxidation by copper(II) salt, removal the trimethylsilyl group. Also, DFT theoretical calculations Marcus theory were employed consolidate proposed mechanism.

Язык: Английский

Процитировано

0