Alcohol Amination with Aminoacidato Cp*Ir(III)-Complexes as Catalysts: Dissociation of the Chelating Ligand during Initiation

被引：28

作者：

Woeckel, Simone ^{[1
]}

Plessow, Philipp ^{[1
,2
]}

Schelwies, Mathias ^{[3
]}

Brinks, Marion K. ^{[3
]}

Rominger, Frank ^{[4
]}

Hofmann, Peter ^{[1
,4
]}

Limbach, Michael ^{[1
,3
]}

机构：

[1] CaRLa Catalysis Res Lab, D-69120 Heidelberg, Germany

[2] BASF SE, Quantum Chem, D-67056 Ludwigshafen, Germany

[3] BASF SE, Synth & Homogenous Catalysis, D-67056 Ludwigshafen, Germany

[4] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

ACS CATALYSIS | 2014年 / 4卷 / 01期

关键词：

alcohol amination; hydrogen borrowing; iridium; sandwich complexes; amino acids; BIOLOGICALLY IMPORTANT LIGANDS; N-HETEROCYCLIC CARBENE; ASTERISK-IR COMPLEX; GAUSSIAN-BASIS SETS; METAL-COMPLEXES; HALFSANDWICH COMPLEXES; TRANSFER HYDROGENATION; EFFICIENT CATALYSTS; ACID COMPLEXES; PRIMARY AMINES;

D O I：

10.1021/cs4009418

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 use of aminoacidato Cp*Ir(III)-complexes in catalytic alcohol amination reactions of primary and secondary alcohols with amines permits to carry out these transformations at very mild reaction conditions without the use of an additional base. Herein we discuss the fate of the chelating aminoacidato ligands upon initiation of Cp*Ir(III)complexes from a mechanistic perspective. Catalyst initiation has been followed by NMR using isotopically labeled C-13,N-15-glycinato complexes.

引用

页码：152 / 161

页数：10

共 74 条

[61] A short history of SHELX [J].

Sheldrick, George M. .

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122

[62] Chemoenzymatic dynamic kinetic resolution of secondary amines [J].

Stirling, Matthew ;

Blacker, John ;

Page, Michael I. .

TETRAHEDRON LETTERS, 2007, 48 (07) :1247-1250

[63] Metal complexes of biologically important ligands, CVII.: Formation of tris(pentamethylcyclopentadienyl-μ-L-prolinato-iridium) tris(trifluoromethanesulfonate) with chiral self recognition [J].

Sünkel, K ;

Hoffmuller, W ;

Beck, W .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1998, 53 (11) :1365-1368

[64] Organic Synthesis Involving Iridium-Catalyzed Oxidation [J].

Suzuki, Takeyuki .

CHEMICAL REVIEWS, 2011, 111 (03) :1825-1845

[65] TRANSITION METAL-CATALYZED N-ALKYLATION OF NH GROUPS OF AZOLES WITH ALCOHOLS [J].

TANAKA, N ;

HATANAKA, M ;

WATANABE, Y .

CHEMISTRY LETTERS, 1992, (04) :575-578

[66] The proton's absolute aqueous enthalpy and Gibbs free energy of solvation from cluster-ion solvation data [J].

Tissandier, MD ;

Cowen, KA ;

Feng, WY ;

Gundlach, E ;

Cohen, MH ;

Earhart, AD ;

Coe, JV ;

Tuttle, TR .

JOURNAL OF PHYSICAL CHEMISTRY A, 1998, 102 (40) :7787-7794

[67] ACCURATE SPIN-DEPENDENT ELECTRON LIQUID CORRELATION ENERGIES FOR LOCAL SPIN-DENSITY CALCULATIONS - A CRITICAL ANALYSIS [J].

VOSKO, SH ;

WILK, L ;

NUSAIR, M .

CANADIAN JOURNAL OF PHYSICS, 1980, 58 (08) :1200-1211

[68] Geometry of coordinatively unsaturated two-legged piano stool complexes with 16 valence electrons: A theoretical study [J].

Ward, TR ;

Schafer, O ;

Daul, C ;

Hofmann, P .

ORGANOMETALLICS, 1997, 16 (14) :3207-3215

[69] Borrowing Hydrogen Methodology for Amine Synthesis under Solvent-Free Microwave Conditions [J].

Watson, Andrew J. A. ;

Maxwell, Aoife C. ;

Williams, Jonathan M. J. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2328-2331

[70] Accurate Coulomb-fitting basis sets for H to Rn [J].

Weigend, F .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2006, 8 (09) :1057-1065

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