1,6-Conjugate hydrogenation of para-quinone methides to phenol-containing diaryl- and triarylmethanes under atmospheric pressure catalyzed by a metal-ligand bifunctional iridium catalyst

被引:4
作者
Zhao, Guoqiang [1 ]
Xu, Xiangchao [1 ]
Zhang, Jin [1 ]
Dong, Beixuan [1 ]
Wang, Wenli [1 ]
Zhou, Wenbo [1 ]
Shi, Qixun [3 ]
Li, Feng [1 ,2 ]
机构
[1] Nanjing Univ Sci & Technol, Sch Chem & Chem Engn, Nanjing 210094, Peoples R China
[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[3] Nanjing Tech Univ, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
基金
中国国家自然科学基金;
关键词
Para -quinone methides; Atmospheric pressure; Qiarylmethanes; Triarylmethanes; Metal-ligand bifunctional catalyst; 1,6 hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; ASTERISK-IR COMPLEX; DEPENDENT TRANSFER HYDROGENATION; SOLUBLE CARBONYL-COMPOUNDS; O-AMINOBENZYL ALCOHOLS; CP-ASTERISK; DEHYDROGENATIVE OXIDATION; BIPYRIDONATE LIGAND; AQUEOUS AMMONIA; N-ALKYLATION;
D O I
10.1016/j.jcat.2024.115812
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The 1,6-conjugate hydrogenation of para-quinone methides to diaryl- and triarylmethanes under atmospheric pressure has been proposed and accomplished. In the presence of [Cp*Ir(2,2 '-bpyO)(H2O)] (0.5 mol %), a range of desirable products were obtained in high yields. Functional groups in bpy ligand were found to be crucially important for the catalytic activity of iridium complexes. Furthermore, the practical application of the present catalytic system was also presented.
引用
收藏
页数:9
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共 104 条
[1]  
Abou Zeid AHS, 2002, FOOD CHEM, V76, P187, DOI 10.1016/S0308-8146(01)00264-3
[2]   New approach to p-hydroxybenzylation of arenes via a quinomethane generated in situ from a Mannich base [J].
Baik, W ;
Lee, HJ ;
Yoo, CH ;
Jung, JW ;
Kim, BH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (05) :587-589
[3]   SYNTHESIS AND STRUCTURE OF [(ETA-C5ME5)IR(CO)]2 [J].
BALL, RG ;
GRAHAM, WAG ;
HEINEKEY, DM ;
HOYANO, JK ;
MCMASTER, AD ;
MATTSON, BM ;
MICHEL, ST .
INORGANIC CHEMISTRY, 1990, 29 (10) :2023-2025
[4]   Hydrogenation of Carboxylic Acids Catalyzed by Half-Sandwich Complexes of Iridium and Rhodium [J].
Brewster, Timothy P. ;
Miller, Alexander J. M. ;
Heinekey, D. Michael ;
Goldberg, Karen I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (43) :16022-16025
[5]   Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: Evidence for concerted hydride and proton transfer [J].
Casey, CP ;
Singer, SW ;
Powell, DR ;
Hayashi, RK ;
Kavana, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1090-1100
[6]   Cp*Ir complex bearing a flexible bridging and functional 2,2′- methylenebibenzimidazole ligand as an auto-tandem catalyst for the synthesis of N-methyl tertiary amines from imines via transfer hydrogenation/N-methylation with methanol [J].
Chen, Xiaozhong ;
Ai, Yao ;
Liu, Peng ;
Yang, Chenchen ;
Yang, Jiazhi ;
Li, Feng .
JOURNAL OF CATALYSIS, 2021, 402 (402) :325-334
[7]   Improved synthesis of the iodine-free thyromimetic GC-1 [J].
Chiellini, G ;
Nguyen, NH ;
Yoshihara, HAI ;
Scanlan, TS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (23) :2607-2611
[8]   Design, Synthesis, and Evaluation of Thyronamine Analogues as Novel Potent Mouse Trace Amine Associated Receptor 1 (mTAAR1) Agonists [J].
Chiellini, Grazia ;
Nesi, Giulia ;
Digiacomo, Maria ;
Malvasi, Rossella ;
Espinoza, Stefano ;
Sabatini, Martina ;
Frascarelli, Sabina ;
Laurino, Annunziatina ;
Cichero, Elena ;
Macchia, Marco ;
Gainetdinov, Raul R. ;
Fossa, Paola ;
Raimondi, Laura ;
Zucchi, Riccardo ;
Rapposelli, Simona .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (12) :5096-5107
[9]   Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers [J].
Chu, Wen-Dao ;
Zhang, Le-Fen ;
Bao, Xu ;
Zhao, Xian-He ;
Zeng, Chao ;
Du, Ji-Yuan ;
Zhang, Guo-Biao ;
Wang, Fang-Xin ;
Ma, Xiao-Yan ;
Fan, Chun-An .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9229-9233
[10]   Discovery, Applications, and Catalytic Mechanisms of Shvo's Catalyst [J].
Conley, Brian L. ;
Pennington-Boggio, Megan K. ;
Boz, Emine ;
Williams, Travis J. .
CHEMICAL REVIEWS, 2010, 110 (04) :2294-2312