Synthesis and odor characteristics of N‐substituted pyrrolyl ketones derived from N‐substituted acetylpyrroles and alcohols DOI
Mingqin Zhao, Jingyi Hu,

Xiaoming Ji

и другие.

Journal of Heterocyclic Chemistry, Год журнала: 2022, Номер 60(4), С. 596 - 605

Опубликована: Дек. 9, 2022

Abstract A transition‐metal and ligand free base‐mediated a radical condensation reaction to form N ‐substituted pyrrolyl ketones with water as the side product is developed. The transformation performed t ‐BuOK, broad range of acetylpyrroles alcohols are well tolerated under optimized conditions. Preliminary studies indicate that anion benzylic alcohol proposed key intermediate, which undergoes coupling enolate acetylpyrrole new CC bond. Subsequently, corresponding chalcones obtained by elimination, enone intermediate reduced afford ketones. odor characteristics were evaluated gas‐chromatography–mass spectrometry–olfactometry (GC–MS–O). present varied characteristic odors, usually distinct from those alcohols. Among them, compounds 3‐cyclopropyl‐1‐(1‐methyl‐1H‐pyrrol‐2‐yl) propan‐1‐one (3c ′ ) 5,9‐dimethyl‐1‐(1‐methyl‐1H‐pyrrol‐2‐yl) dec‐8‐en‐1‐one (3g not decomposed high temperature, according results pyrolysis–GC/MS.

Язык: Английский

Alcohols as Substrates in Transition-Metal-Catalyzed Arylation, Alkylation, and Related Reactions DOI

Adam Cook,

Stephen G. Newman

Chemical Reviews, Год журнала: 2024, Номер 124(9), С. 6078 - 6144

Опубликована: Апрель 17, 2024

Alcohols are abundant and attractive feedstock molecules for organic synthesis. Many methods their functionalization require them to first be converted into a more activated derivative, while recent years have seen vast increase in the number of complexity-building transformations that directly harness unprotected alcohols. This Review discusses how transition metal catalysis can used toward this goal. These broadly classified three categories. Deoxygenative functionalizations, representing derivatization C–O bond, enable alcohol act as leaving group formation new C–C bonds. Etherifications, characterized by O–H represent classical reactivity has been modernized include mild reaction conditions, diverse partners, high selectivities. Lastly, chain reactions described, wherein acts mediator formal C–H alkyl backbone. Each these classes transformation will discussed context intermolecular arylation, alkylation, related reactions, illustrating alcohols harnessed

Язык: Английский

Процитировано

35

Upgrading Ethanol to n-Butanol in the Presence of Carbonate Catalyzed by a Cp*Ir Complex Bearing a Functional 2,2′-Carbonylbibenzimidazole Ligand DOI
Xiangchao Xu, Jin Zhang, Beixuan Dong

и другие.

Inorganic Chemistry, Год журнала: 2024, Номер 63(8), С. 3843 - 3849

Опубликована: Фев. 14, 2024

Upgrading ethanol to n-butanol as biofuels is an important topic for sustainable chemistry. Herein, a Cp*Ir complex bearing functional 2,2′-carbonylbibenzimidazole ligand [Cp*Ir(2,2′-COBiBzImH2)Cl][Cl] was designed and synthesized. In the presence of catalyst (0.1 mol %) Cs2CO3 (6 %), highest yield updated up 37% with 80% selectivity. NH units in are crucially catalytic activity iridium complex.

Язык: Английский

Процитировано

10

Auto-Tandem Catalyst: From Allylic Alcohols to Secondary Alcohols via Redox Isomerization/Atmospheric Hydrogenation in Water Catalyzed by a Water-Soluble Iridium Complex Bearing a Functional Ligand DOI
Xiaozhong Chen, Beixuan Dong,

Guoqiang Zhao

и другие.

Inorganic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 13, 2025

A water-soluble iridium complex [Cp*Ir(6,6′-(OH)2-2,2′-bpy)(H2O)][OTf]2 was found to be an efficient autotandem catalyst for the synthesis of secondary alcohols via redox isomerization/atmospheric hydrogenation in water. The OH groups bpy ligand are a key factor activity catalyst. Then, mechanistic experiments and practical utilization catalytic system were presented.

Язык: Английский

Процитировано

1

From hydrogen autotransfer process to deuterium autotransfer process: The N-trideuteromethylation of amines with deuterated methanol to trideuteromethylated amines catalyzed by a Cp*Ir complex bearing a flexible bridging and functional ligand DOI
Peng Liu, Xiaozhong Chen, Xiangchao Xu

и другие.

Journal of Catalysis, Год журнала: 2022, Номер 410, С. 333 - 338

Опубликована: Апрель 25, 2022

Язык: Английский

Процитировано

30

Recent Advances for Alkylation of Ketones and Secondary Alcohols Using Alcohols in Homogeneous Catalysis DOI

Dongyuan Yang,

Hongli Wang, Chun‐Ran Chang

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(18), С. 3100 - 3121

Опубликована: Июль 4, 2022

Abstract The alkylation of ketones or secondary alcohols using as alkylating agents via hydrogen borrowing strategy presents a powerful method for the synthesis ɑ‐alkylated ketones. In this review, we summarize progress catalyzed by Ir, Pd, Rh, Ru, Mn, Fe, Co, Ni, and Cu catalysts α‐alkylation with cross‐coupling from 2017 to 2021. A wide range (aromatic aliphatic ketones) (benzylic primary alcohols, aromatic alkenyl diols) are well tolerated. Furthermore, also discuss current challenges propose perspectives on coming development in filed. objective present review is give an overview recent advances β‐alkylation alcohols. Finally, hope that will inspirations magnified image

Язык: Английский

Процитировано

29

Direct use of methanol instead of formaldehyde or paraformaldehyde: Acceptorless dehydrogenative coupling for the synthesis of arylhydrazones catalyzed by a metal–ligand iridium bifunctional catalyst DOI
Beixuan Dong,

Yiqian He,

Xiangchao Xu

и другие.

Journal of Catalysis, Год журнала: 2024, Номер 438, С. 115685 - 115685

Опубликована: Авг. 3, 2024

Язык: Английский

Процитировано

5

Selective N-Alkylation of Aminobenzenesulfonamides with Alcohols for the Synthesis of Amino-(N-alkyl)benzenesulfonamides Catalyzed by a Metal–Ligand Bifunctional Ruthenium Catalyst DOI

Lu Shen,

Xingliang Wu,

Lili Shi

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8397 - 8406

Опубликована: Июнь 3, 2024

[(

Процитировано

4

Direct couplings of secondary alcohols with primary alkenyl alcohols to α-alkylated ketones via a tandem transfer hydrogenation/hydrogen autotransfer process catalyzed by a metal-ligand bifunctional iridium catalyst DOI
Xiangchao Xu, Shun Li,

Shiyuan Luo

и другие.

Journal of Catalysis, Год журнала: 2022, Номер 413, С. 365 - 373

Опубликована: Июнь 25, 2022

Язык: Английский

Процитировано

19

A recyclable covalent triazine framework-supported iridium(iii) terpyridine complex for the acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to form quinolines DOI
Xiaozhong Chen, Yao Ai, Deyun Liu

и другие.

Materials Chemistry Frontiers, Год журнала: 2022, Номер 6(9), С. 1228 - 1235

Опубликована: Янв. 1, 2022

A complex Ir(tpy)@CTF, which is synthesized by the coordinative immobilization of [Ir(tpy)Cl 3 ] on a covalent triazine framework, was proven to be recycle catalyst for acceptorless dehydrogenative coupling o -aminobenzyl alcohols with ketones.

Язык: Английский

Процитировано

17

Quinoline-derived NNP-manganese complex catalyzed α-alkylation of ketones with primary alcohols DOI
Peidong Song,

Hao‐Jie Rong,

Tingting Meng

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(25), С. 5112 - 5116

Опубликована: Янв. 1, 2024

An air-stable quinoline-derived NNP ligand chelated Mn catalyst was developed for the efficient α-alkylation of ketones with primary alcohols

Язык: Английский

Процитировано

3