Ru(II)-Catalyzed C-H Activation and Annulation Reaction via Carbon-Carbon Triple Bond Cleavage

被引：43

作者：

Prakash, Rashmi ^{[1
]}

Bora, Bidisha R. ^{[1
]}

Boruah, Romesh C. ^{[1
]}

Gogoi, Sanjib ^{[1
]}

机构：

[1] CSIR North East Inst Sci & Technol, Appl Organ Chem Chem Sci & Technol Div, AcSIR, Jorhat 785006, Assam, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 08期

关键词：

CATALYZED CLEAVAGE; ALKYNE; FUNCTIONALIZATION; HYDROAMINATION; CONSTRUCTION; QUINAZOLINE; INDOLES; ALKENE;

D O I：

10.1021/acs.orglett.8b00643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented Ru(II)-catalyzed C-H activation and annulation reaction, which proceeds via C-C triple bond cleavage, is reported. This reaction of 2-phenyldihydrophthalazinediones with alkynes, which works most efficiently in the presence of bidented ligand 1,3-bis(diphenylphosphino)propane, affords good yields of substituted quinazolines.

引用

页码：2297 / 2300

页数：4

共 40 条

[1] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles [J].

Ackermann, Lutz ;

Potukuchi, Harish K. ;

Landsberg, Dirk ;

Vicente, Ruben .

ORGANIC LETTERS, 2008, 10 (14) :3081-3084

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

Ackermann, Lutz .

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

[3] Design, synthesis, and biological activity of prazosin-related antagonists.: Role of the piperazine and furan units of prazosin on the selectivity for α1-adrenoreceptor subtypes [J].

Bolognesi, ML ;

Budriesi, R ;

Chiarini, A ;

Poggesi, E ;

Leonardi, A ;

Melchiorre, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4844-4853

[4] Poly(p-phenyleneethynylene)s by alkyne metathesis [J].

Bunz, UHF .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (12) :998-1010

[5]

Bunz UHF, 1999, ANGEW CHEM INT EDIT, V38, P478, DOI 10.1002/(SICI)1521-3773(19990215)38:4<478::AID-ANIE478>3.0.CO

[6]

2-K

[7] Reaction of [W(eta(2)-PhC(2)Ph)(3)(NCMe)] with o-diphenylphosphino-styrene and -allylbenzene; Evidence for novel carbon-carbon double and triple bond cleavage and alkyne insertion reactions [J].

Cairns, GA ;

Carr, N ;

Green, M ;

Mahon, MF .

CHEMICAL COMMUNICATIONS, 1996, (21) :2431-2432

[8] Ethylene and alkyne carbon-carbon bond cleavage across tungsten-tungsten multiple bonds [J].

Chamberlin, RLM ;

Rosenfeld, DC ;

Wolczanski, PT ;

Lobkovsky, EB .

ORGANOMETALLICS, 2002, 21 (13) :2724-2735

[9] Gold-catalyzed oxidative cleavage of aryl-substituted alkynyl ethers using molecular oxygen. Simultaneous degradation of C-H and single and triple carbon-carbon bonds under ambient conditions [J].

Das, Arindam ;

Chaudhuri, Rupsha ;

Liu, Rai-Shung .

CHEMICAL COMMUNICATIONS, 2009, (27) :4046-4048

[10] A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide [J].

Datta, S ;

Chang, CL ;

Yeh, KL ;

Liu, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9294-9295

← 1 2 3 4 →