One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant

被引：4

作者：

Muratov, Karim ^{[1
]}

Afanasyev, Oleg, I ^{[1
]}

Kuchuk, Ekaterina ^{[1
]}

Runikhina, Sofiya ^{[1
]}

Chusov, Denis ^{[1
,2
]}

机构：

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

[2] GV Plekhanov Russian Univ Econ, 36 Stremyanny Per, Moscow 117997, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 38期

基金：

俄罗斯科学基金会;

关键词：

Aldehydes; Ketones; Tertiary amines; Secondary amines; Carbon monoxide; RUTHENIUM-CATALYZED SYNTHESIS; N-ALKYLATION; UNACTIVATED OLEFINS; ALCOHOLS; HYDROAMINOMETHYLATION; TRIBENZYLAMINE; HYDROAMINATION; COMPLEX;

D O I：

10.1002/ejoc.201901175

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh-catalyzed one-step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69-83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62-79 % yields.

引用

页码：6557 / 6560

页数：4

共 44 条

[31] Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions
Ruiz-Castillo, Paula
Buchwald, Stephen L.
[J]. CHEMICAL REVIEWS, 2016, 116 (19) : 12564 - 12649
[32] Indenyl rhodium complexes. Synthesis and catalytic activity in reductive amination using carbon monoxide as a reducing agent
Runikhina, Sofiya A.
Arsenov, Mikhail A.
Kharitonov, Vladimir B.
Sovdagarova, Elizaveta R.
Chusova, Olga
Nelyubina, Yulia V.
Denisov, Gleb L.
Usanov, Dmitry L.
Chusov, Denis
Loginov, Dmitry A.
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 867 : 106 - 112
[33] Photo- and electroactive amorphous molecular materials - molecular design, syntheses, reactions, properties, and applications
Shirota, Y
[J]. JOURNAL OF MATERIALS CHEMISTRY, 2005, 15 (01) : 75 - 93
[34] Organic materials for electronic and optoelectronic devices
Shirota, Y
[J]. JOURNAL OF MATERIALS CHEMISTRY, 2000, 10 (01) : 1 - 25
[35] An improved and one-pot procedure to the synthesis of symmetric amines by domino reactions of 5-methyl-1,3,4-thiadiazole-2-amine, a new nitrogen atom donor, and alkyl halides
Soleiman-Beigi, Mohammad
Mohammadi, Fariba
[J]. MONATSHEFTE FUR CHEMIE, 2017, 148 (12): : 2123 - 2128
[36] Selective palladium-catalyzed arylation of ammonia: Synthesis of anilines as well as symmetrical and unsymmetrical Di- and triarylamines
Surry, David S.
Buchwald, Stephen L.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (34) : 10354 - +
[37] Total synthesis of (±)-aspidospermidine
Toczko, MA
Heathcock, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) : 2642 - 2645
[38] Multicomponent synthesis of tertiary alkylamines by photocatalytic olefin-hydroaminoalkylation
Trowbridge, Aaron
Reich, Dominik
Gaunt, Matthew J.
[J]. NATURE, 2018, 561 (7724) : 522 - 527
[39] Catalytic Asymmetric Reductive Condensation of N-H Imines: Synthesis of C2-Symmetric Secondary Amines
Wakchaure, Vijay N.
List, Benjamin
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (51) : 15775 - 15778
[40] Rational development of practical catalysts for aromatic carbon-nitrogen bond formation
Wolfe, JP
Wagaw, S
Marcoux, JF
Buchwald, SL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) : 805 - 818

← 1 2 3 4 5 →