Copper catalyzed oxidative deamination of Betti bases: an efficient approach for benzoylation/formylation of naphthols and phenols

被引：35

作者：

Deb, Mohit L. ^{[1
]}

Pegu, Choitanya Dev ^{[1
]}

Borpatra, Paran J. ^{[1
]}

Baruah, Pranjal K. ^{[1
]}

机构：

[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India

来源：

RSC ADVANCES | 2016年 / 6卷 / 46期

关键词：

C-H BOND; DEHYDROGENATIVE COUPLING REACTIONS; SURFACTANT-COMBINED CATALYST; MANNICH-TYPE REACTIONS; FRIES REARRANGEMENT; TERTIARY-AMINES; ENANTIOSELECTIVE ADDITION; BENZOPHENONE DERIVATIVES; MULTICOMPONENT SYNTHESIS; FACILE SYNTHESIS;

D O I：

10.1039/c6ra04567g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.

引用

页码：40552 / 40559

页数：8

共 152 条

[51] Oxidative Coupling of Tertiary Amines: Scope, Mechanism and Challenges [J].

Jones, Kevin M. ;

Klussmann, Martin .

SYNLETT, 2012, (02) :159-162

[52] Catalytic methods for C-H bond functionalization: Application in organic synthesis [J].

Kakiuchi, F ;

Chatani, N .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (9-10) :1077-1101

[53] Catalytic C-H/olefin coupling [J].

Kakiuchi, F ;

Murai, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :826-834

[54] Fries rearrangement at atmospheric pressure using microwave irradiation. [J].

Khadilkar, BM ;

Madyar, VR .

SYNTHETIC COMMUNICATIONS, 1999, 29 (07) :1195-1200

[55] A FACILE SYNTHESIS OF 1,4-DIHYDRO-1-ALKYL-2H-3,1-BENZOXAZINES AND RELATED-COMPOUNDS [J].

KIENZLE, F .

TETRAHEDRON LETTERS, 1983, 24 (21) :2213-2216

[56] Catalytic Oxidative Coupling Reactions for the Formation of Carbon-Carbon Bonds without Carbon-Metal Intermediates [J].

Klussmann, Martin ;

Sureshkumar, Devarajulu .

SYNTHESIS-STUTTGART, 2011, (03) :353-369

[57] THE CATALYTIC FRIES REARRANGEMENT OF ACYLOXY NAPHTHALENES USING SCANDIUM TRIFLUOROMETHANESULFONATE AS A CATALYST [J].

KOBAYASHI, S ;

MORIWAKI, M ;

HACHIYA, I .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (15) :1527-1528

[58] Hafnium trifluoromethanesulfonate (Hf(OTf)4) as an efficient catalyst in the fries rearrangement and direct acylation of phenol and naphthol derivatives [J].

Kobayashi, S ;

Moriwaki, M ;

Hachiya, I .

TETRAHEDRON LETTERS, 1996, 37 (12) :2053-2056

[59] Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis [J].

Krick, Anja ;

Kehraus, Stefan ;

Gerhaeuser, Clarissa ;

Klimo, Karin ;

Nieger, Martin ;

Maier, Armin ;

Fiebig, Heinz-Herbert ;

Atodiresei, Iuliana ;

Raabe, Gerhard ;

Fleischhauer, Joerg ;

Koenig, Gabriele M. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (03) :353-360

[60] Micelle promoted supramolecular carbohydrate scaffold-catalyzed multicomponent synthesis of 1,2-dihydro-1-aryl-3H-naphth[1,2-e][1,3]oxazin-3-one and amidoalkyl naphthols derivatives in aqueous medium [J].

Kumar, Atul ;

Gupta, Maneesh Kumar ;

Kumar, Mukesh .

RSC ADVANCES, 2012, 2 (19) :7371-7376

← 1 2 3 4 5 6 7 8 9 10 →