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：0

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

来源：

JOURNAL OF CATALYSIS | 2024年 / 440卷

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

页数：9

共 11 条

[1] Recyclable Bismuth Complex Catalyzed 1,6-Conjugate Addition of Various Nucleophiles to para-Quinone Methides: Expedient Access to Unsymmetrical Diaryl- and Triarylmethanes
Liang, Xianghao
Xu, Haiyan
Li, Hanlin
Chen, Lizhuang
Lu, Hongfei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (02) : 217 - 226
[2] Asymmetric 1,6-Conjugate Addition of para-Quinone Methides for the Synthesis of Chiral β,β-Diaryl-α-Hydroxy Ketones
Gao, Yuan-Yuan
Hua, Yuan-Zhao
Wang, Min-Can
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (01) : 80 - 85
[3] Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides
Zhang, Xiang-Zhi
Deng, Yu-Hua
Yan, Xu
Yu, Ke-Yin
Wang, Fang-Xin
Ma, Xiao-Yan
Fan, Chun-An
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5655 - 5662
[4] Hydrogenation of Quinones to Hydroquinones under Atmospheric Pressure Catalyzed by a Metal-Ligand Bifunctional Iridium Catalyst
Zhang, Jin
Xu, Xiangchao
Zhao, Guoqiang
You, Heng
Wang, Rongzhou
Li, Feng
ORGANIC LETTERS, 2024, 26 (09) : 1857 - 1862
[5] Ligand-Free Copper-Catalyzed 1,6-Conjugate Reaction of para-Quinone Methides with gem-Diborylalkanes
He, Jing
Meng, Deyuan
Lee, Dong Yeon
Yun, Jaesook
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (47)
[6] Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles
Deng, Yu-Hua
Zhang, Xiang-Zhi
Yu, Ke-Yin
Yan, Xu
Du, Ji-Yuan
Huang, Hanmin
Fan, Chun-An
CHEMICAL COMMUNICATIONS, 2016, 52 (22) : 4183 - 4186
[7] An efficient Fe(III)-catalyzed 1,6-conjugate addition of para-quinone methides with fluorinated silyl enol ethers toward β,β-diaryl α-fluorinated ketones
Hao, Yong-Jia
Hu, Xiao-Si
Yu, Jin-Sheng
Zhou, Feng
Zhou, Ying
Zhou, Jian
TETRAHEDRON, 2018, 74 (52) : 7395 - 7398
[8] Metal-Free, Acid-Catalyzed 1,6-Conjugate Addition of NH-Sulfoximines to para-Quinone Methides: Accessing to Diarylmethine Imino Sulfanone
More, Satish G.
Rupanawar, Bapurao D.
Suryavanshi, Gurunath
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (15): : 10129 - 10139
[9] Bi(OTf)3 Catalyzed Solvent Free Approach to Unsymmetrical Diaryl(2-indolyl) methanes through 1,6-Conjugate Addition of 3-Substituted Indoles to para-Quinone Methides
Goswami, Prithwish
Anand, Ramasamy Vijaya
CHEMISTRYSELECT, 2016, 1 (10): : 2556 - 2559
[10] Ambient-pressure highly active hydrogenation of ketones and aldehydes catalyzed by a metal-ligand bifunctional iridium catalyst under base-free conditions in water
Wang, Rongzhou
Yue, Yuancheng
Qi, Jipeng
Liu, Shiyuan
Song, Ao
Zhuo, Shuping
Xing, Ling-Bao
JOURNAL OF CATALYSIS, 2021, 399 : 1 - 7

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