Sequential C-C σ-Bond Cleavage/(sp2) C-O Bond Formation via C-H Functionalization toward Pyranoindolones Fused with Medium-Sized Rings

被引：25

作者：

Wang, Mengdan ^{[1
]}

Kong, Lingkai ^{[1
]}

Wang, Ye ^{[1
]}

Song, Bo ^{[1
]}

Sun, Yue ^{[1
]}

Tang, Rong ^{[1
]}

Li, Yanzhong ^{[1
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 500 Dongchuan Rd, Shanghai 200241, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 19期

基金：

中国国家自然科学基金;

关键词：

PROMOTED TANDEM REACTION; CHROMONE DERIVATIVES; SELECTIVE FUNCTIONALIZATION; ORGANOMETALLIC CHEMISTRY; EFFICIENT SYNTHESIS; INSERTION REACTION; ROOM-TEMPERATURE; SINGLE-BOND; CARBON; ACTIVATION;

D O I：

10.1021/acs.orglett.8b02580

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An atom-economical procedure for the synthesis of pyranoindolones fused with 7- or 8-membered rings has been developed. This process is realized through the sequential Cs2CO3-promoted C-C sigma-bond cleavage of cyclic ketoesters and a ZnI2-mediated selective C-H/O-H coupling reaction. Two of the C-C sigma-bonds are cleaved and one of the sp(2) C-H bonds is functionalized during the reaction process. Easily accessible starting materials and broad substrate scope make this protocol attractive in synthetic organic chemistry.

引用

页码：6130 / 6134

页数：5

共 50 条

[1] Ruthenium(II)-Catalysed sp2 C-H Bond Functionalization by C-C Bond Formation
Li, Bin
Dixneuf, Pierre H.
RUTHENIUM IN CATALYSIS, 2014, 48 : 119 - 193
[2] Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
Fan, Xiaohui
Cui, Xiao-Meng
Guan, Yong-Hong
Fu, Lin-An
Lv, Hao
Guo, Kun
Zhu, Hong-Bo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 498 - 501
[3] C-C Bond formation via double C-H functionalization
DeBoef, Brenton
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[4] C-C Bond formation via double C-H functionalization
DeBoef, Brenton
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[5] Micellar Catalysis as a Tool for C-H Bond Functionalization toward C-C Bond Formation
Borrego, Elena
Caballero, Ana
Perez, Pedro J.
ORGANOMETALLICS, 2022, 41 (22) : 3084 - 3098
[6] Direct Sequential C-O and C-C Formation via Double sp2 C-H Bond Activations to Construct 6H-Benzo[c]chromen-6-ones
Sun, Chang-Liang
Liu, Jia
Wang, Yang
Zhou, Xiao
Li, Bi-Jie
Shi, Zhang-Jie
SYNLETT, 2011, (07) : 883 - 886
[7] Catalytic C-C Bond Formation by C-H Functionaliza C-C Bond Cleavage Preface
Dong, Guangbin
TETRAHEDRON, 2016, 72 (22) : 2717 - 2717
[8] Cu(II)-Mediated C-C/C-O Bond Formation via C-H/C-C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
Yu, Shuling
Lv, Ningning
Liu, Zhanxiang
Zhang, Yuhong
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (01) : 118 - 125
[9] 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
[10] Recent advancements in metal-free C-C bond formation via C-H bond functionalization
Sikder, Ankita
Sengupta, Jhimli
ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (11) : 2539 - 2571

← 1 2 3 4 5 →