CH2 Linkage Effects on the Reactivity of Bis(aminophosphine)-Ruthenium Complexes for Selective Hydrogenation of Esters into Alcohols

被引：10

作者：

Fang, Xiaolong ^{[1
]}

Sun, Mingjun ^{[2
]}

Zheng, Jianwei ^{[1
]}

Li, Bin ^{[1
]}

Ye, Linmin ^{[1
]}

Wang, Xiaoping ^{[1
]}

Cao, Zexing ^{[2
]}

Zhu, Hongping ^{[1
]}

Yuan, Youzhu ^{[1
]}

机构：

[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Natl Engn Lab Green Chem Prod Alcohols Ethers Est, Coll Chem & Chem Engn,iChEM, Xiamen 361005, Peoples R China

[2] Xiamen Univ, Coll Chem & Chem Engn, State Key Lab Phys Chem Solid Surfaces, Fujian Prov Key Lab Theoret & Computat Chem, Xiamen 361005, Peoples R China

来源：

SCIENTIFIC REPORTS | 2017年 / 7卷

关键词：

CATALYTIC-HYDROGENATION; CHEMOSELECTIVE HYDROGENATION; NONCOVALENT INTERACTIONS; RUTHENIUM COMPLEXES; CARBONYL-COMPOUNDS; DESIGN; REDUCTION; KETONES; ACTIVATION; EFFICIENCY;

D O I：

10.1038/s41598-017-04362-9

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

A novel ruthenium complex binding to two subtly different aminophosphine ligands, (o-PPh2C6H4CH2NH2)(o-PPh2C6H4NH2)RuCl2, was successfully isolated. This bis(aminophosphine)ruthenium complex shows efficient activity in both dimethyl oxalate (DMO) and methyl benzoate (MB) hydrogenation. On the contrast, similar complexes (o-PPh2C6H4NH2)(2)RuCl2 and (o-PPh2C6H4CH2NH2)(2)RuCl2, can only effectively catalyze the hydrogenation of DMO and MB, respectively. Our experimental studies in combination of theoretical calculations reveal that the remarkable substrate selectivity in the hydrogenation of esters arises from the nonbonding interactions operated by the CH2 linkage of the ligand.

引用

页数：9

共 54 条

[1] Synthesis of ruthenium hydride complexes containing beta-aminophosphine ligands derived from amino acids and their use in the H2-hydrogenation of ketones and imines [J].

Abdur-Rashid, K ;

Guo, RW ;

Lough, AJ ;

Morris, RH ;

Song, DT .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :571-579

[2] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].

Austin, JF ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173

[3] Design Strategies for Enhanced Hydrogen- Bond Donor Catalysts [J].

Auvil, Tyler J. ;

Schafer, Andrew G. ;

Mattson, Anita E. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (13) :2633-2646

[4] Mild and selective hydrogenation of aromatic and aliphatic (di) nitriles with a well-defined iron pincer complex [J].

Bornschein, Christoph ;

Werkmeister, Svenja ;

Wendt, Bianca ;

Jiao, Haijun ;

Alberico, Elisabetta ;

Baumann, Wolfgang ;

Junge, Henrik ;

Junge, Kathrin ;

Beller, Matthias .

NATURE COMMUNICATIONS, 2014, 5

[5] Iron-Based Catalysts for the Hydrogenation of Esters to Alcohols [J].

Chakraborty, Sumit ;

Dai, Huiguang ;

Bhattacharya, Papri ;

Fairweather, Neil T. ;

Gibson, Michael S. ;

Krause, Jeanette A. ;

Guan, Hairong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) :7869-7872

[6] Recent developments in the homogeneous hydrogenation of carboxylic acid esters [J].

Clarke, Matthew L. .

CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (12) :2418-2423

[7] Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope [J].

Copeland, GT ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) :6496-6502

[8] Use of achiral (diphosphine)RuCl2(diamine) precatalysts as a practical alternative to sodium borohydride for ketone reduction [J].

de Koning, Pieter D. ;

Jackson, Mark ;

Lennon, Ian C. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) :1054-1058

[9] Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen [J].

Dub, Pavel A. ;

Ikariya, Takao .

ACS CATALYSIS, 2012, 2 (08) :1718-1741

[10] A SET OF F-POLARIZATION FUNCTIONS FOR PSEUDO-POTENTIAL BASIS-SETS OF THE TRANSITION-METALS SC-CU, Y-AG AND LA-AU [J].

EHLERS, AW ;

BOHME, M ;

DAPPRICH, S ;

GOBBI, A ;

HOLLWARTH, A ;

JONAS, V ;

KOHLER, KF ;

STEGMANN, R ;

VELDKAMP, A ;

FRENKING, G .

CHEMICAL PHYSICS LETTERS, 1993, 208 (1-2) :111-114

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