Mild and general conditions for the cross-coupling of aryl halides with pentafluorobenzene and other perfluoroaromatics

被引：194

作者：

Lafrance, Marc ^{[1
]}

Shore, Daniel ^{[1
]}

Fagnou, Keith ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 22期

关键词：

PALLADIUM-CATALYZED ARYLATION; C-H ACTIVATION; LIQUID-CRYSTALLINE; EFFICIENT; DISCOVERY;

D O I：

10.1021/ol0619967

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.

引用

页码：5097 / 5100

页数：4

共 39 条

[11] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[12] Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C-H activation [J].

Huang, QH ;

Fazio, A ;

Dai, GX ;

Campo, MA ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7460-7461

[13] Synthesis and properties of new light-emitting polymers containing fluorinated tetraphenyl units [J].

Hwang, DH ;

Song, SY ;

Ahn, T ;

Chu, HY ;

Do, LM ;

Kim, SH ;

Shim, HK ;

Zyung, T .

SYNTHETIC METALS, 2000, 111 :485-487

[14] 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

[15] A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage [J].

Kakiuchi, F ;

Kan, S ;

Igi, K ;

Chatani, N ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1698-1699

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

Kakiuchi, F ;

Murai, S .

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

[17] Oxidative C-H activation/C-C bond forming reactions: Synthetic scope and mechanistic insights [J].

Kalyani, D ;

Deprez, NR ;

Desai, LV ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7330-7331

[18] Fluorinated aromatics as sensitizers for photo-splitting of water [J].

Kitamura, T ;

Wada, Y ;

Yanagida, S .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 105 (02) :305-311

[19] Suzuki-Miyaura coupling reaction using pentafluorophenylboronic acid [J].

Korenaga, T ;

Kosaki, T ;

Fukumura, R ;

Ema, T ;

Sakai, T .

ORGANIC LETTERS, 2005, 7 (22) :4915-4917

[20] Catalytic intermolecular direct arylation of perfluorobenzenes [J].

Lafrance, Marc ;

Rowley, Christopher N. ;

Woo, Tom K. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (27) :8754-8756

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