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
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
收藏
页码:1055 / 1057
页数:3
相关论文
共 50 条
[41]   Iridium-catalyzed reductive amination of carboxylic acids [J].
Ouyang, Lu ;
Miao, Rui ;
Yang, Zhanhui ;
Luo, Renshi .
JOURNAL OF CATALYSIS, 2023, 418 :283-289
[42]   An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols [J].
Tuan Thanh Dang ;
Ramalingam, Balamurugan ;
Shan, Siah Pei ;
Seayad, Abdul Majeed .
ACS CATALYSIS, 2013, 3 (11) :2536-2540
[43]   Catalytic -Alkylation/Reduction of Ketones with Primary Alcohols To Furnish Secondary Alcohols [J].
Lundberg, Helena ;
Adolfsson, Hans .
SYNTHESIS-STUTTGART, 2016, 48 (05) :644-652
[44]   Iridium-CNP complex catalyzed cross-coupling of primary alcohols and secondary alcohols by a borrowing hydrogen strategy [J].
Wang, Dawei ;
Zhao, Keyan ;
Yu, Xin ;
Miao, Hongyan ;
Ding, Yuqiang .
RSC ADVANCES, 2014, 4 (81) :42924-42929
[45]   Iridium-Catalyzed C5-Regioselective Esterification of Dienyl Alcohols with Carboxylic Acids [J].
Chen, Jiadong ;
Zhang, Yulu ;
Tang, Shengbiao ;
Shao, Ying ;
Sun, Jiangtao .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (32)
[46]   Enantioselective Carbonyl Propargylation by Iridium-Catalyzed Transfer Hydrogenative Coupling of Alcohols and Propargyl Chlorides [J].
Woo, Sang Kook ;
Geary, Laina M. ;
Krische, Michael J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (31) :7830-7834
[47]   Enantioselective Synthesis of Alcohols and Amines by Iridium-Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes [J].
Bartoszewicz, Agnieszka ;
Ahlsten, Nanna ;
Martin-Matute, Belen .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (23) :7274-7302
[48]   Manganese-Catalyzed Chemoselective Coupling of Secondary Alcohols, Primary Alcohols and Methanol [J].
Tang, Jun ;
He, Jingxi ;
Zhao, Sheng-Yin ;
Liu, Weiping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (17)
[49]   Iridium catalyzed alkylation of 2′-hydroxyacetophenone with alcohols under thermal or microwave conditions [J].
Hunter, Jamie ;
Rice, Scott ;
Lowe, Robert ;
Pask, Christopher M. ;
Warriner, Stuart ;
Sridharan, Visuvanathar .
TETRAHEDRON LETTERS, 2017, 58 (46) :4400-4402
[50]   Iridium-Catalyzed Vinylation of Carbazole Derivatives with Vinyl Acetate [J].
Kimura, Jungo ;
Nakamichi, Seiya ;
Ogawa, Shinji ;
Obora, Yasushi .
SYNLETT, 2017, 28 (06) :719-723