Iridium-catalyzed α-Alkylation of Acetonitrile with Primary and Secondary Alcohols

被引：50

作者：

Sawaguchi, Takuya ^{[1
]}

Obora, Yasushi ^{[1
]}

机构：

[1] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Osaka 5648680, Japan

来源：

CHEMISTRY LETTERS | 2011年 / 40卷 / 09期

关键词：

ONE-POT SYNTHESIS; OXIDATIVE CONVERSION; HIGHLY EFFICIENT; BETA-ALKYLATION; PRIMARY AMINES; TETRABUTYLAMMONIUM PEROXYDISULFATE; BORROWING HYDROGEN; ORGANIC-SYNTHESIS; COUPLING REACTION; CARBOXYLIC-ACIDS;

D O I：

10.1246/cl.2011.1055

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acetonitrile is successfully alkylated with primary and secondary alcohols in the presence of t-BuOK using [Ir(OH)(cod)](2) as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chemistry.

引用

页码：1055 / 1057

页数：3

共 50 条

[11] Highly Efficient Base Catalyzed N-alkylation of Amines with Alcohols and β-Alkylation of Secondary Alcohols with Primary Alcohols [J].

Garg, Nitish K. ;

Tan, Mattias ;

Johnson, Magnus T. ;

Wendt, Ola F. .

CHEMCATCHEM, 2023, 15 (20)

[12] Efficient Iron-Catalyzed Direct ß-Alkylation of Secondary Alcohols with Primary Alcohols [J].

Yang, Jian ;

Liu, Xin ;

Meng, Da-Li ;

Chen, Hong-Yan ;

Zong, Zhi-Hui ;

Feng, Ting-Ting ;

Sun, Kai .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (2-3) :328-334

[13] Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols [J].

Onoda, Mitsuki ;

Fujita, Ken-ichi .

ORGANIC LETTERS, 2020, 22 (18) :7295-7299

[14] Room temperature and solvent-free iridium-catalyzed selective alkylation of anilines with alcohols [J].

Li, Jia-Qi ;

Andersson, Pher G. .

CHEMICAL COMMUNICATIONS, 2013, 49 (55) :6131-6133

[15] Iridium-Catalyzed Oxidative Methyl Esterification of Primary Alcohols and Diols with Methanol [J].

Yamamoto, Nobuyuki ;

Obora, Yasushi ;

Ishii, Yasutaka .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08) :2937-2941

[16] Iridium-catalyzed reaction of enones with alcohols affording 1,3-diketones [J].

Obora, Yasushi ;

Nakamura, Kazuhiro ;

Hatanaka, Shintaro .

CHEMICAL COMMUNICATIONS, 2012, 48 (53) :6720-6722

[17] Iridium-Pyrazolato Complex Catalyzed Dehydrogenative Alkylation of Ketones and Arylacetonitriles with Primary Alcohols [J].

Panda, Surajit ;

Maharana, Suraj Kumar ;

Saha, Ratnakar ;

Bagh, Bidraha .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (48)

[18] The Synthesis of Benzimidazoles and Quinoxalines from Aromatic Diamines and Alcohols by Iridium-Catalyzed Acceptorless Dehydrogenative Alkylation [J].

Hille, Toni ;

Irrgang, Torsten ;

Kempe, Rhett .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (19) :5569-5572

[19] Tris(acetylacetonato)rhodium(III)-Catalyzed α-Alkylation of Ketones, β-Alkylation of Secondary Alcohols and Alkylation of Amines with Primary Alcohols [J].

Satyanarayana, Ponnam ;

Reddy, Ganapam Manohar ;

Maheswaran, Hariharasharma ;

Kantam, Mannepalli Lakshmi .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1859-1867

[20] One-pot β-alkylation of secondary alcohols with primary alcohols catalyzed by ruthenacycles [J].

Chang, Xu ;

Chuan, Low Wei ;

Yongxin, Li ;

Pullarkat, Sumod A. .

TETRAHEDRON LETTERS, 2012, 53 (12) :1450-1455

← 1 2 3 4 5 →