Iron-Catalyzed Tandem Three-Component Alkylation: Access to α-Methylated Substituted Ketones

被引：61

作者：

Bettoni, Leo ^{[1
]}

Seck, Charlotte ^{[1
,2
]}

Mbaye, Mbaye Diagne ^{[1
,2
]}

Gaillard, Sylvain ^{[1
]}

Renaud, Jean-Luc ^{[1
]}

机构：

[1] Normandie Univ, LCMT, ENSICAEN, UNICAEN,CNRS, 6 Blvd Marechal Juin, F-14000 Caen, France

[2] Univ Assane Seck Ziguinchor, BP 523, Ziguinchor, Senegal

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 09期

关键词：

TRANSITION-METAL-COMPLEXES; LIGAND-EXCHANGE REACTION; BORROWING HYDROGEN; METHANOL; ALCOHOLS; DEHYDROGENATION; DEMETALATION; AMINES; BONDS;

D O I：

10.1021/acs.orglett.9b00630

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The borrowing hydrogen strategy has been applied in the synthesis of alpha-branched methylated ketones via a tandem three-component reaction catalyzed by a diaminocyclopentadienone iron tricarbonyl complex. Various alkyl and aromatic methyl ketones underwent dialkylation with various primary alcohols and methanol as alkylating agents in mild reaction conditions and good yields. Deuterium labeling experiments suggested that the benzylic alcohol was the hydrogen source in this tandem process.

引用

页码：3057 / 3061

页数：5

共 46 条

[1] The Methylation Effect in Medicinal Chemistry [J].

Barreiro, Eliezer J. ;

Kuemmerle, Arthur E. ;

Fraga, Carlos A. M. .

CHEMICAL REVIEWS, 2011, 111 (09) :5215-5246

[2] Manganese catalyzed α-methylation of ketones with methanol as a C1 source [J].

Bruneau-Voisine, Antoine ;

Pallova, Lenka ;

Bastin, Stephanie ;

Cesar, Vincent ;

Sortais, Jean-Baptiste .

CHEMICAL COMMUNICATIONS, 2019, 55 (03) :314-317

[3]

Caine D., 1991, Comprehensive Organic Synthesis, V3, P1, DOI DOI 10.1016/B978-0-08-052349-1.00058-5

[4] Utilization of MeOH as a C1 Building Block in Tandem Three Component Coupling Reaction [J].

Chakrabarti, Kaushik ;

Maji, Milan ;

Panja, Dibyajyoti ;

Paul, Bhaskar ;

Shee, Sujan ;

Das, Gourab Kanti ;

Kundu, Sabuj .

ORGANIC LETTERS, 2017, 19 (18) :4750-4753

[5] Rhodium-Catalyzed Ketone Methylation Using Methanol Under Mild Conditions: Formation of α-Branched Products [J].

Chan, Louis K. M. ;

Poole, Darren L. ;

Shen, Di ;

Healy, Mark P. ;

Donohoe, Timothy J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) :761-765

[6] Ruthenium and osmium complexes in C-C bond-forming reactions by borrowing hydrogen catalysis [J].

Chelucci, Giorgio .

COORDINATION CHEMISTRY REVIEWS, 2017, 331 :1-36

[7] Advances in One-Pot Synthesis through Borrowing Hydrogen Catalysis [J].

Corma, Avelino ;

Navas, Javier ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2018, 118 (04) :1410-1459

[8] Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2-Hydroxypyridylmethylene Fragment [J].

Deng, Danfeng ;

Hu, Bowen ;

Yang, Min ;

Chen, Dafa .

ORGANOMETALLICS, 2018, 37 (19) :3353-3359

[9] Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].

Dobereiner, Graham E. ;

Crabtree, Robert H. .

CHEMICAL REVIEWS, 2010, 110 (02) :681-703

[10] OXIDATION OF ALCOHOLS BY TRANSITION-METAL COMPLEXES .5. SELECTIVE CATALYTIC MONOALKYLATION OF ARYLACETONITRILES BY ALCOHOLS [J].

GRIGG, R ;

MITCHELL, TRB ;

SUTTHIVAIYAKIT, S ;

TONGPENYAI, N .

TETRAHEDRON LETTERS, 1981, 22 (41) :4107-4110

← 1 2 3 4 5 →