tert-Butyl peroxybenzoate (TBPB)-mediated 2-isocyanobiaryl insertion with 1,4-dioxane: efficient synthesis of 6-alkyl phenanthridines via C(sp3)-H/C(sp2)-H bond functionalization

被引：127

作者：

Cao, Jia-Jia ^{[1
]}

Zhu, Tong-Hao ^{[1
]}

Wang, Shun-Yi ^{[1
]}

Gu, Zheng-Yang ^{[1
]}

Wang, Xiang ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 49期

基金：

中国国家自然科学基金;

关键词：

CARBON-HYDROGEN BONDS; C-H ACTIVATION; OXIDATIVE CYCLIZATION; COUPLING REACTIONS; O BOND; ARYLATION; SUBSTITUTION; DERIVATIVES; ETHERS; ISONITRILES;

D O I：

10.1039/c4cc00743c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the construction of 6- alkyl phenanthridines by tert- butyl peroxybenzoate (TBPB)- mediated 2- isocyanobiaryl insertion with 1,4- dioxane was established. Two new C- C bonds were formed in this reaction via a sequential C(sp(3))-H/C(sp(2))-H bond functionalization under metal-free conditions.

引用

页码：6439 / 6442

页数：4

共 51 条

[1] New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense
Abdel-Halim, OB
Morikawa, T
Ando, S
Matsuda, H
Yoshikawa, M
[J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07): : 1119 - 1124
[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
Ackermann, Lutz
Vicente, Ruben
Kapdi, Anant R.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
[3] Molecular determinants for DNA minor groove recognition: Design of a bis-guanidinium derivative of ethidium that is highly selective for AT-rich DNA sequences
Bailly, C
Arafa, RK
Tanious, FA
Laine, W
Tardy, C
Lansiaux, A
Colson, P
Boykin, DW
Wilson, WD
[J]. BIOCHEMISTRY, 2005, 44 (06) : 1941 - 1952
[4] An azido-hanessian reaction
Baruah, M
Bols, M
[J]. SYNLETT, 2002, (07) : 1111 - 1112
[5] Nickel(0)/NaHMDS adduct-mediated intramolecular alkylation of unactivated arenes via a homolytic aromatic substitution mechanism
Beaulieu, Louis-Philippe B.
Roman, Daniela Sustac
Vallee, Frederic
Charette, Andre B.
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (66) : 8249 - 8251
[6] KOtBu Mediated Synthesis of Phenanthridinones and Dibenzoazepinones
Bhakuni, Bhagat Singh
Kumar, Amit
Balkrishna, Shah Jaimin
Sheikh, Javeed Ahmed
Konar, Sanjit
Kumar, Sangit
[J]. ORGANIC LETTERS, 2012, 14 (11) : 2838 - 2841
[7] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction
Chen, Long
Shi, Erbo
Liu, Zhaojun
Chen, Shulin
Wei, Wei
Li, Hong
Xu, Kai
Wan, Xiaobing
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) : 4085 - 4089
[8] Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes
Chen, Wen-Ching
Hsu, Yu-Chen
Shih, Wei-Chun
Lee, Ching-Yu
Chuang, Wen-Han
Tsai, Yi-Fang
Chen, Peter Ping-Yu
Ong, Tiow-Gan
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (53) : 6702 - 6704
[9] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
Chen, Xiao
Engle, Keary M.
Wang, Dong-Hui
Yu, Jin-Quan
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
[10] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
Daugulis, Olafs
Do, Hien-Quang
Shabashov, Dmitry
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086

← 1 2 3 4 5 6 →