Facile Synthesis of 3,3′-Disubstituted 2,2′-Binaphthyls by Transition-metal-catalyzed Double Benzannulation

被引：15

作者：

Umeda, Rui ^{[1
]}

Tabata, Hiromasa ^{[1
]}

Tobe, Yoshito ^{[2
]}

Nishiyama, Yutaka ^{[1
]}

机构：

[1] Kansai Univ, Fac Chem Mat & Bioengn, Osaka 5648680, Japan

[2] Osaka Univ, Grad Sch Engn Sci, Osaka 5608531, Japan

来源：

CHEMISTRY LETTERS | 2014年 / 43卷 / 06期

关键词：

ALKYNES; ACID;

D O I：

10.1246/cl.140169

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3,3'-Disubstituted 2,2'-binaphthyls were prepared by the Cu-or Re-catalyzed double benzannulation reaction of 2-(phenylethynyl)benzaldehydewith various butadiynes in the presence of trichloroacetic acid, in moderate to good yields. Acceleration of the second benzannulation was clearly observed.

引用

页码：883 / 884

页数：2

共 50 条

[1] A new route to 2,2′,3,3′-tetrasubstituted binaphthyls
Widhalm, Michael
Aichinger, Christian
Mereiter, Kurt
TETRAHEDRON LETTERS, 2009, 50 (20) : 2425 - 2429
[2] Transition-Metal-Catalyzed [3+2+2] Cycloaddition Reactions
Kuila, Bilash
Kaur, Maninderjeet
Singh, Prabhpreet
Bhargava, Gaurav
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (07) : 853 - 868
[3] 3,3'-DISUBSTITUTED 2,2'-BIPHENOLS - SYNTHESIS OF NONPLANAR, TETRADENTATE CHELATING LIGANDS
SORRELL, TN
ELLIS, DJ
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26): : 5765 - 5769
[4] SELECTIVE CROSS-COUPLING OF 2-NAPHTHOL AND 2-NAPHTHYLAMINE DERIVATIVES - A FACILE SYNTHESIS OF 2,2',3-TRISUBSTITUTED AND 2,2',3,3'-TETRASUBSTITUTED 1,1'-BINAPHTHYLS
SMRCINA, M
VYSKOCIL, S
MACA, B
POLASEK, M
CLAXTON, TA
ABBOTT, AP
KOCOVSKY, P
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08): : 2156 - 2163
[5] Regiocontrolled one-step synthesis of 3,3′-disubstituted 2,2′-bipyridine ligands by cobalt(I)-catalyzed cyclotrimerization
Varela, JA
Castedo, L
Maestro, M
Mahía, J
Saá, C
CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (23) : 5203 - 5213
[6] A FACILE SYNTHESIS OF 2,2'-BIPYRIDYL-3,3'-DICARBOXYLIC ACID
WIMMER, FL
WIMMER, S
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (05) : 368 - 369
[7] Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling
Zhao, Xiao-Jing
Li, Zi-Hao
Ding, Tong-Mei
Tian, Jin-Miao
Tu, Yong-Qiang
Wang, Ai-Fang
Xie, Yu-Yang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 7061 - 7065
[8] Synthesis of poly(2,2′,3,3′-indole)
Shagun, L. G.
Dorofeev, I. A.
Smirnov, V. I.
Tokareva, I. A.
Voronkov, M. G.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (12) : 2360 - 2362
[9] Synthesis of poly(2,2′,3,3′-indole)
L. G. Shagun
I. A. Dorofeev
V. I. Smirnov
I. A. Tokareva
M. G. Voronkov
Russian Chemical Bulletin, 2012, 61 : 2360 - 2362
[10] Advances in transition-metal-catalyzed synthesis of 3-substituted isocoumarins
Saeed, Aamer
Haroon, Mehfooz
Muhammad, Faisal
Larik, Fayaz Ali
El-Seedi, Hesham
Channar, Pervaiz Ali
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 834 : 88 - 103

← 1 2 3 4 5 →