Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes

被引：39

作者：

Qi, Bing ^{[1
]}

Guo, Shan ^{[1
]}

Zhang, Wenjing ^{[1
]}

Yu, Xiaolong ^{[1
]}

Song, Chao ^{[1
]}

Zhu, Jin ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Coordinat Chem, Sch Chem & Chem Engn, Dept Polymer Sci & Engn, Nanjing 210023, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 13期

基金：

中国国家自然科学基金;

关键词：

N-N BOND; SELECTIVE SYNTHESIS; CATALYZED SYNTHESIS; AEROBIC OXIDATION; H/O-H; FUNCTIONALIZATION; ACCESS; ANNULATION; ALKYNES; INDOLES;

D O I：

10.1021/acs.orglett.8b01563

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Rh(III)-catalyzed enaminone-directed alkenyl C-H coupling with alkynes for the synthesis of salicylaldehyde derivatives is reported. This represents a unique example of benzene ring framework formation through a transition-metal-catalyzed, directed C-H activation strategy. The two incorporated reactive functionalities, aldehyde and hydroxy groups, provide convenient synthetic handles for further structural elaboration.

引用

页码：3996 / 3999

页数：4

共 83 条

[1] Versatile Synthesis of Isocoumarins and α-Pyrones by Ruthenium-Catalyzed Oxidative C-H/O-H Bond Cleavages [J].

Ackermann, Lutz ;

Pospech, Jola ;

Graczyk, Karolina ;

Rauch, Karsten .

ORGANIC LETTERS, 2012, 14 (03) :930-933

[2] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].

Ackermann, Lutz ;

Fenner, Sabine .

ORGANIC LETTERS, 2011, 13 (24) :6548-6551

[3] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[4]

Balali E., 2013, ORIENT J CHEM, V29, P1611, DOI 10.13005/ojc/290445

[5] Bimetallic Cu-Pd Nanoparticles Supported on Bio-silica as an Efficient Catalyst for Selective Aerobic Oxidation of Benzylic Alcohols [J].

Buxaderas, Eduardo ;

Graziano-Mayer, Marilyn ;

Alicia Volpe, Maria ;

Radivoy, Gabriel .

SYNTHESIS-STUTTGART, 2017, 49 (06) :1387-1393

[6] Construction of Diverse and Functionalized 2H-Chromenes by Organocatalytic Multicomponent Reactions [J].

Cai, Hongyun ;

Xia, Likai ;

Lee, Yong Rok ;

Shim, Jae-Jin ;

Kim, Sung Hong .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) :5212-5220

[7] Rhodium(III)-Catalyzed N-Nitroso-Directed C-H Addition to Ethyl 2-Oxoacetate for Cycloaddition/Fragmentation Synthesis of Indazoles [J].

Chen, Jinsen ;

Chen, Pei ;

Song, Chao ;

Zhu, Jin .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) :14245-14249

[8] Catalytic Silylation of Unactivated C-H Bonds [J].

Cheng, Chen ;

Hartwig, John F. .

CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975

[9] Catalytic reduction by formic acid under pressure - Part I The preparation of aldehydes from carboxylic acids with titanium dioxide as catalyst [J].

Davies, RR ;

Hodgson, HH .

JOURNAL OF THE CHEMICAL SOCIETY, 1943, :84-86

[10] Copper catalyzed oxidative deamination of Betti bases: an efficient approach for benzoylation/formylation of naphthols and phenols [J].

Deb, Mohit L. ;

Pegu, Choitanya Dev ;

Borpatra, Paran J. ;

Baruah, Pranjal K. .

RSC ADVANCES, 2016, 6 (46) :40552-40559

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