C-C coupling reactions of superstrong CF3 groups with C(sp2)-H bonds:: Reactivity and synthetic utility of zero-valent niobium catalyst

被引：30

作者：

Fuchibe, Kohei ^{[1
]}

Mitomi, Ken ^{[1
]}

Suzuki, Ryo ^{[1
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2008年 / 3卷 / 02期

关键词：

carbenoids; C-C coupling; C-F activation; C-H activation; niobium;

D O I：

10.1002/asia.200700333

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It was found that zero-valent niobium is an efficient catalyst for the intramolecular C-C coupling reactions of o-aryl and o-alkenyl alpha,alpha,alpha-trifluorotoluene derivatives. The superstrong C-F bonds of CF3 groups and neighboring C(sp(2))-H bonds were doubly activated, and fluorenes and indenes were obtained in good yields. The niobium fluorocarbenoid species is proposed to be the key intermediate.

引用

页码：261 / 271

页数：11

共 50 条

[1] Reductive Cleavage of C(sp2)-CF3 Bonds in Trifluoromethylpyridines
Onge, Piers St.
Khan, Shajia I.
Cook, Adam
Newman, Stephen G.
ORGANIC LETTERS, 2023, 25 (06) : 1030 - 1034
[2] Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds
Wang, Chang-Sheng
Dixneuf, Pierre H.
Soule, Jean-Francois
CHEMICAL REVIEWS, 2018, 118 (16) : 7532 - 7585
[3] Highly stable magnetically separable copper nanocatalyst as an efficient catalyst for C(sp2)-C(sp) and C(sp2)-C(sp2) cross-coupling reactions
Keypour, Hassan
Balali, Masomeh
Nejat, Razieh
Bagherzadeh, Mojtaba
APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (09)
[4] Cross-Coupling Reactions between C(sp2)-H and C(sp3)-H Bonds via Sequential Dehydrogenation and C-H Insertion
Kuninobu, Yoichiro
Asanoma, Daisuke
Takai, Kazuhiko
SYNLETT, 2010, (19) : 2883 - 2886
[5] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups
Rouquet, Guy
Chatani, Naoto
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) : 11726 - 11743
[6] Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective
Gui, Yong-Yuan
Liao, Li-Li
Sun, Liang
Zhang, Zhen
Ye, Jian-Heng
Shen, Guo
Lu, Zhi-Peng
Zhou, Wen-Jun
Yu, Da-Gang
CHEMICAL COMMUNICATIONS, 2017, 53 (06) : 1192 - 1195
[7] Challenges in C-C bond formation through direct transformations of sp2 C-H bonds
Yu, Da-Gang
Li, Bi-Jie
Shi, Zhang-Jie
TETRAHEDRON, 2012, 68 (26) : 5130 - 5136
[8] Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds
Li, Yaqiong
Fan, Yuhang
Jia, Qianfa
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 350 - 362
[9] Rhodium(III)-Catalyzed Oxidative Cross-Coupling of Unreactive C(sp3)-H Bonds with C(sp2)-H Bonds
Tan, Guangying
You, Jingsong
ORGANIC LETTERS, 2017, 19 (18) : 4782 - 4785
[10] Oxidative coupling between C(sp2)-H and C(sp3)-H bonds of indoles and cyclic ethers/cycloalkanes
Yang, Qingjing
Choy, Pui Ying
Wu, Yinuo
Fan, Baomin
Kwong, Fuk Yee
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (09) : 2608 - 2612

← 1 2 3 4 5 →