Palladium-Catalyzed intramolecular C-H Activation/C-C Bond Formation: A Straightforward Synthesis of Phenanthridines

被引：81

作者：

Peng, Jinsong ^{[1
,2
]}

Chen, Tonghui ^{[1
]}

Chen, Chunxia ^{[1
]}

Li, Bin ^{[1
,2
]}

机构：

[1] NE Forestry Univ, Dept Chem & Chem Engn, Coll Sci, Harbin 150040, Peoples R China

[2] NE Forestry Univ, Postdoctoral Mobile Res Stn Forestry Engn, Harbin 150040, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 22期

基金：

中国博士后科学基金;

关键词：

6-SUBSTITUTED PHENANTHRIDINES; MEDIATED SYNTHESIS; DIRECT ARYLATION; CONVENIENT SYNTHESIS; BENZYNE CYCLIZATION; DERIVATIVES; MECHANISM; ISOQUINOLINES; CONSTRUCTION; ACYLOXIMES;

D O I：

10.1021/jo2017108

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed intramolecular C-H activation/C-C cross-coupling has been developed for a straightforward and efficient synthesis of phenanthridines. With Pd(OAc)(2) (4 mol %) as the catalyst, PCy3 (8 mol %) as the ligand, and Cs2CO3 as the base, this protocol was applied to synthesize a small library of phenanthridine derivatives in good yields in THF.

引用

页码：9507 / 9513

页数：7

共 51 条

[41] Microwave-assisted syntheses of n-heterocycles using alkenone-, alkynone- and aryl-carbonyl O-phenyl oximes:: Formal synthesis of neocryptolepine [J].

Portela-Cubillo, Fernando ;

Scoto, Jackie S. ;

Walton, John C. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) :5558-5565

[42] Synthesis of phenanthridines by radical C-aryl-C-aryl coupling [J].

Rosa, AM ;

Lobo, AM ;

Branco, PS ;

Prabhakar, S ;

Pereira, AMDL .

TETRAHEDRON, 1997, 53 (01) :269-284

[43] Functionalized phenanthridine and dibenzopyranone derivatives through benzyne cyclization -: Application to the total syntheses of trisphaeridine and N-methylcrinasiadine [J].

Sanz, Roberto ;

Fernandez, Yolanda ;

Castroviejo, M. Pilar ;

Perez, Antonio ;

Fananas, Francisco J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) :62-69

[44] Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines [J].

Shabashov, Dmitry ;

Daugulis, Olafs .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7720-7725

[45] Cascade approach to substituted 6-aryl-phenanthridines from aromatic aldehydes, anilines, and benzenediazonium-2-carboxylate [J].

Shou, Wang-Ge ;

Yang, Yun-Yun ;

Wang, Yan-Guang .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9241-9243

[46] Phenanthridine synthesis via [2+2+2] cyclotrimerization reactions [J].

Sripada, Lakshminath ;

Teske, Jesse A. ;

Deiters, Alexander .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (02) :263-265

[47] Two color RNA intercalating probe for cell imaging applications [J].

Stevens, Nathan ;

O'Connor, Naphtali ;

Vishwasrao, Harshad ;

Samaroo, Diana ;

Kandel, Eric R. ;

Akins, Daniel L. ;

Drain, Charles M. ;

Turro, Nicholas J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7182-+

[48] An ammonia equivalent for the palladium-catalyzed amination of aryl halides and triflates [J].

Wolfe, JP ;

Ahman, J ;

Sadighi, JP ;

Singer, RA ;

Buchwald, SL .

TETRAHEDRON LETTERS, 1997, 38 (36) :6367-6370

[49] Indium(III)-catalyzed tandem reaction with alkynylbenzaldehydes and alkynylanilines to heteroaromatic compounds [J].

Yanada, Reiko ;

Hashimoto, Kana ;

Tokizane, Rie ;

Miwa, Yoshihisa ;

Minami, Hideki ;

Yanada, Kazuo ;

Ishikura, Minoru ;

Takemoto, Yoshiji .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5135-5138

[50] Trifluoroacetic acid-mediated facile construction of 6-substituted phenanthridines [J].

Youn, So Won ;

Bihn, Joon Hyung .

TETRAHEDRON LETTERS, 2009, 50 (32) :4598-4601

← 1 2 3 4 5 6 →