Phosphine ligands in the ruthenium-catalyzed reductive amination without an external hydrogen source

被引：6

作者：

Makarova, Maria ^{[1
]}

Afanasyev, Oleg I. ^{[1
]}

Kliuev, Fedor ^{[2
]}

Nelyubina, Yulia V. ^{[1
]}

Godovikova, Maria ^{[1
]}

Chusov, Denis ^{[1
,2
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova St 28, Moscow 119991, Russia

[2] Natl Res Univ Higher Sch Econ, Miasnitskaya Str 20, Moscow 101000, Russia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2021年 / 941卷

基金：

俄罗斯科学基金会;

关键词：

Ruthenium; Phosphines; Reductive amination; Carbon monoxide; Catalysis; COMPLEXES; CHEMISTRY; ALDEHYDES; AMINES;

D O I：

10.1016/j.jorganchem.2021.121806

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A systematic study of the phosphine additives influence on the activity of a ruthenium catalyst in reductive amination without an external hydrogen source was carried out. [CymeneRuCl(2)](2) was used as a reference catalyst, and a broad set of phosphines including Alk(3)P, Alk(2)ArP, Ar3P and X3P was screened. Three complexes of general formula (Cymene)RuCl2PR3 were isolated in a pure form, and their catalytic activity was compared with the in situ generated complexes. Nonhindered triarylphosphines with electron acceptor groups were found to be the most perspective activating agents, increasing the activity of the catalyst approx. six times, Alk(2)ArP ligands have less noticeable influence, while trialkylphosphines strongly deactivate the ruthenium catalyst. (C) 2021 Elsevier B.V. All rights reserved.

引用

页数：8

共 55 条

[1] Symmetrical Tertiary Amines: Applications and Synthetic Approaches [J].

Afanasyev, Oleg, I ;

Kuchuk, Ekaterina A. ;

Muratov, Karim M. ;

Denisov, Gleb L. ;

Chusov, Denis .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (04) :543-586

[2] Direct Reductive Amination of Camphor Using Iron Pentacarbonyl as Stoichiometric Reducing Agent: Features and Limitations [J].

Afanasyev, Oleg I. ;

Fatkulin, Artemy R. ;

Solyev, Pavel N. ;

Smirnov, Ivan ;

Amangeldyev, Artem ;

Semenov, Sergey E. ;

Chusov, Denis .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (39) :6289-6294

[3] Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family [J].

Afanasyev, Oleg, I ;

Podyacheva, Evgeniya ;

Rudenko, Alexander ;

Tsygankov, Alexey A. ;

Makarova, Maria ;

Chusov, Denis .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) :9347-9360

[4] Alkyl formates as reagents for reductive amination of carbonyl compounds [J].

Afanasyev, Oleg I. ;

Cherkashehenko, Ilia ;

Kuznetsov, Anton ;

Kliuev, Fedor ;

Semenov, Sergey ;

Chusova, Olga ;

Denisova, Gleb ;

Chusov, Denis .

MENDELEEV COMMUNICATIONS, 2020, 30 (01) :112-113

[5] Reductive Amination in the Synthesis of Pharmaceuticals [J].

Afanasyev, Oleg, I ;

Kuchuk, Ekaterina ;

Usanov, Dmitry L. ;

Chusov, Denis .

CHEMICAL REVIEWS, 2019, 119 (23) :11857-11911

[6] Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent [J].

Afanasyev, Oleg I. ;

Usanov, Dmitry L. ;

Chusov, Denis .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (48) :10164-10166

[7] Cyclobutadiene Metal Complexes: A New Class of Highly Selective Catalysts. An Application to Direct Reductive Amination [J].

Afanasyev, Oleg I. ;

Tsygankov, Alexey A. ;

Usanov, Dmitry L. ;

Perekalin, Dmitry S. ;

Shvydkiy, Nikita V. ;

Maleev, Victor I. ;

Kudinov, Alexander R. ;

Chusov, Denis .

ACS CATALYSIS, 2016, 6 (03) :2043-2046

[8] Preparation and reactivity of p-cymene complexes of ruthenium and osmium incorporating 1,3-triazenide ligands [J].

Albertin, Gabriele ;

Antoniutti, Stefano ;

Castro, Jesus ;

Paganelli, Stefano .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2010, 695 (18) :2142-2152

[9] Harnessing the Power of the Water-Gas Shift Reaction for Organic Synthesis [J].

Ambrosi, Andrea ;

Denmark, Scott E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12164-12189

[10] Development of new methods in modern selective organic synthesis: preparation of functionalized molecules with atomic precision [J].

Ananikov, V. P. ;

Khemchyan, L. L. ;

Ivanova, Yu V. ;

Bukhtiyarov, V. I. ;

Sorokin, A. M. ;

Prosvirin, I. P. ;

Vatsadze, S. Z. ;

Medved'ko, A. V. ;

Nuriev, V. N. ;

Dilman, A. D. ;

Levin, V. V. ;

Koptyug, I. V. ;

Kovtunov, K. V. ;

Zhivonitko, V. V. ;

Likholobov, V. A. ;

Romanenko, A. V. ;

Simonov, P. A. ;

Nenajdenko, V. G. ;

Shmatova, I. ;

Muzalevskiy, V. M. ;

Nechaev, M. S. ;

Asachenko, A. F. ;

Morozov, S. ;

Dzhevakov, P. B. ;

Osipov, S. N. ;

Vorobyeva, D. V. ;

Topchiy, M. A. ;

Zotova, M. A. ;

Ponomarenko, S. A. ;

Borshchev, V. ;

Luponosov, Yu N. ;

Rempel, A. A. ;

Valeeva, A. A. ;

Stakheev, A. Yu. ;

Turov, V. ;

Mashkovsky, I. S. ;

Sysolyatin, S. V. ;

Malykhin, V. V. ;

Bukhtiyarova, G. A. ;

Terent'ev, A. O. ;

Krylov, I. B. .

RUSSIAN CHEMICAL REVIEWS, 2014, 83 (10) :885-985

← 1 2 3 4 5 6 →