Iron-Catalyzed Cross-Coupling of N-Heterocyclic Chlorides and Bromides with Arylmagnesium Reagents

被引：79

作者：

Kuzmina, Olesya M. ^{[1
]}

Steib, Andreas K. ^{[1
]}

Flubacher, Dietmar ^{[2
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Novartis Pharma AG, CH-4056 Basel, Switzerland

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 18期

基金：

欧洲研究理事会;

关键词：

ARYL GRIGNARD-REAGENTS; SECONDARY ALKYL-HALIDES; BETA-HYDROGENS; BOND FORMATION; COMPLEX; TOSYLATES; EFFICIENT; OXIDANT; LIGAND; SALTS;

D O I：

10.1021/ol302136c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, practical iron salt catalyzed procedure allows fast cross-couplings of N-heterocyclic chlorides and bromides with various electron-rich and -poor arylmagnesium reagents. A solvent mixture of THF and tBuOMe is found to be essential for achieving high yields mainly by avoiding homocoupling side reactions.

引用

页码：4818 / 4821

页数：4

共 77 条

[41] Kumada-Tamao-Corriu Coupling of Alkyl Halides Catalyzed by an Iron-Bisphosphine Complex
Hatakeyama, Takuji
Fujiwara, Yu-ichi
Okada, Yoshihiro
Itoh, Takuma
Hashimoto, Toru
Kawamura, Shintaro
Ogata, Kazuki
Takaya, Hikaru
Nakamura, Masaharu
[J]. CHEMISTRY LETTERS, 2011, 40 (09) : 1030 - 1032
[42] Iron-Catalyzed Suzuki-Miyaura Coupling of Alkyl Halides
Hatakeyama, Takuji
Hashimoto, Toru
Kondo, Yoshiyuki
Fujiwara, Yuichi
Seike, Hirofumi
Takaya, Hikaru
Tamada, Yoshinori
Ono, Teruo
Nakamura, Masaharu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (31) : 10674 - 10676
[43] Iron-Catalyzed Negishi Coupling Toward an Effective Olefin Synthesis
Hatakeyama, Takuji
Nakagawa, Naohisa
Nakamura, Masaharu
[J]. ORGANIC LETTERS, 2009, 11 (20) : 4496 - 4499
[44] Highly Selective Biaryl Cross-Coupling Reactions between Aryl Halides and Aryl Grignard Reagents: A New Catalyst Combination of N-Heterocyclic Carbenes and Iron, Cobalt, and Nickel Fluorides
Hatakeyama, Takuji
Hashimoto, Sigma
Ishizuka, Kentaro
Nakamura, Masaharu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) : 11949 - 11963
[45] Iron-Catalyzed Enyne Cross-Coupling Reaction
Hatakeyama, Takuji
Yoshimoto, Yuya
Gabriel, Toma
Nakamura, Masaharu
[J]. ORGANIC LETTERS, 2008, 10 (23) : 5341 - 5344
[46] Iron-Catalyzed Cross-Coupling of Alkyl Sulfonates with Arylzinc Reagents
Ito, Shingo
Fujiwara, Yu-ichi
Nakamura, Eiichi
Nakamura, Masaharu
[J]. ORGANIC LETTERS, 2009, 11 (19) : 4306 - 4309
[47] Iron-catalyzed Chemoselective Cross-coupling of α-Bromocarboxylic Acid Derivatives with Aryl Grignard Reagents
Jin, Masayoshi
Nakamura, Masaharu
[J]. CHEMISTRY LETTERS, 2011, 40 (09) : 1012 - 1014
[48] The first iron-catalysed aluminium-variant Negishi coupling: critical effect of co-existing salts on the dynamic equilibrium of arylaluminium species and their reactivity
Kawamura, Shintaro
Ishizuka, Kentaro
Takaya, Hikaru
Nakamura, Masaharu
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (33) : 6054 - 6056
[49] Factors determining the course and mechanisms of Grignard reactions. IV. The effect of metallic halides on the reaction of aryl Grignard reagents and organic halides
Kharasch, MS
Fields, EK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1941, 63 : 2316 - 2320
[50] Iron-catalyzed aryl-aryl cross-coupling reaction tolerating amides and unprotected quinolinones
Kofink, Christiane C.
Blank, Benoit
Pagano, Sandro
Goetz, Nadine
Knochel, Paul
[J]. CHEMICAL COMMUNICATIONS, 2007, (19) : 1954 - 1956

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