RHODIUM-CATALYZED SYNTHESIS OF BENZOFURANS BY THE REACTION OF KETONES AND O-DIFLUOROBENZENES

被引：5

作者：

Arisawa, Mieko ^{[1
]}

Nakane, Soichiro ^{[1
]}

Kuwajima, Manabu ^{[1
]}

Yamaguchi, Masahiko ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

HETEROCYCLES | 2012年 / 86卷 / 02期

关键词：

Benzofuran; o-Difluorobenzene; Polyfluorinated Benzofuran; Rhodium-Catalyzed Reaction; alpha-Arylation; ONE-POT SYNTHESIS; ALPHA-ARYLATION; INHIBITORS; OLIGOSTILBENES; DERIVATIVES; CHEMISTRY;

D O I：

10.3987/COM-12-S(N)57

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of catalytic amounts of RhH(PPh3)(4) and 1,2-bis(diphenylphosphino)ethane (dppe), ketones reacted with o-difluorobenzenes giving benzofurans in high yields. The alpha-arylation of ketones and furan cyclization proceeded without using a base. Benzofuran cyclization was applied to substituted pentafluorobenzenes to give 6-substituted-4,5,7-trifluorobenzofuranes.

引用

页码：1103 / 1118

页数：16

共 50 条

[31] Traceless Rhodium-Catalyzed Hydroacylation Using Alkyl Aldehydes: The Enantioselective Synthesis of -Aryl Ketones
Bouisseau, Anais
Gao, Ming
Willis, Michael C.
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (44) : 15624 - 15628
[32] Synthesis of α,β-Unsaturated Ketones by Rhodium-Catalyzed Carbonylative Arylation of Internal Alkynes with Arylboronic Acids
Kus, Melih
Artok, Oezge Aksin
Ziyanak, Firat
Artok, Levent
SYNLETT, 2008, (17) : 2587 - 2592
[33] Synthesis of Benzofurans via Tandem Rhodium-Catalyzed C(sp3)-H Insertion and Copper-Catalyzed Dehydrogenation
Li, Lin
Xia, Xiao-Han
Wang, Yong
Bora, Pranjal P.
Kang, Qiang
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (09) : 2089 - 2097
[34] Rhodium-catalyzed enantioselective reductive aldol reaction
Taylor, SJ
Duffey, MO
Morken, JP
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) : 4528 - 4529
[35] The rhodium-catalyzed Pauson-Khand reaction
Kobayashi, T
Koga, Y
Narasaka, K
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 73 - 87
[36] A Scalable Rhodium-Catalyzed Intermolecular Aziridination Reaction
Smith, David T.
Njardarson, Jon T.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (17) : 4278 - 4280
[37] Rhodium-catalyzed addition of arylboron compounds to nitriles, ketones, and imines
Ueura, Kenji
Miyamura, Sawako
Satoh, Tetsuya
Miura, Masahiro
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (12) : 2821 - 2826
[38] Enantioselective Rhodium-Catalyzed Addition of Arylboronic Acids to Trifluoromethyl Ketones
Luo, Renshi
Li, Ke
Hu, Yuling
Tang, Wenjun
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) : 1297 - 1302
[39] Rhodium-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of α-Nitro Ketones
Sun, Hao
Xu, Liren
Ruan, Sai
Ratovelomanana-Vidal, Virginie
Chen, Gen-Qiang
Zhang, Xumu
ORGANIC LETTERS, 2024, 26 (46) : 10008 - 10012
[40] Rhodium-catalyzed Reformatsky-type reaction
Kanai, K
Wakabayashi, H
Honda, T
ORGANIC LETTERS, 2000, 2 (16) : 2549 - 2551

← 1 2 3 4 5 →