Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

被引：49

作者：

Wang, Binjie ^{[1
]}

Liu, Yue ^{[1
]}

Lin, Cong ^{[1
]}

Xu, Yiming ^{[1
]}

Liu, Zhanxiang ^{[1
]}

Zhang, Yuhong ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 17期

关键词：

INTRAMOLECULAR DIRECT ARYLATION; C-H FUNCTIONALIZATION; DIRECTING GROUPS; ORGANIC SEMICONDUCTORS; BOND ACTIVATION; SIMPLE ARENES; DERIVATIVES; THIOETHERS; SULFOXIDES; DIBENZOTHIOPHENES;

D O I：

10.1021/ol502127j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

引用

页码：4574 / 4577

页数：4

共 50 条

[1] Synthesis of Fluorenone Derivatives through Pd-Catalyzed Dehydrogenative Cyclization
Li, Hu
Zhu, Ru-Yi
Shi, Wen-Juan
He, Ke-Han
Shi, Zhang-Jie
[J]. ORGANIC LETTERS, 2012, 14 (18) : 4850 - 4853
[2] Novel synthesis of bridged phenylthienylethenes and dithienylethenes via Pd-catalyzed double-cyclization reactions of diarylhexadienynes
Rahman, SMA
Sonoda, M
Ono, M
Miki, K
Tobe, Y
[J]. ORGANIC LETTERS, 2006, 8 (06) : 1197 - 1200
[3] Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C-H activation
Huang, QH
Fazio, A
Dai, GX
Campo, MA
Larock, RC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) : 7460 - 7461
[4] Preparation of Dibenzofurotropones via Pd-Catalyzed Cyclization
Lin, Yu-Wei
Liu, Shiuh-Tzung
[J]. REACTIONS, 2024, 5 (01): : 111 - 119
[5] Synthesis of Bridged Biaryl Atropisomers via Sequential Cu- and Pd-Catalyzed Asymmetric Ring Opening and Cyclization
Xue, Xiaoping
Gu, Zhenhua
[J]. ORGANIC LETTERS, 2019, 21 (11) : 3942 - 3945
[6] Synthesis of sterically congested bicyclic tetrahydrofurans via Pd-catalyzed cyclization
Shin, Chul
Oh, Youna
Cha, Joo Hwan
Pae, Ae Nim
Choo, Hyunah
Cho, Yong Seo
[J]. TETRAHEDRON, 2007, 63 (10) : 2182 - 2190
[7] Synthesis of substituted oxazoles via Pd-catalyzed tandem oxidative cyclization
Zhang, Wei
Yu, Wenlong
Yan, Qiangqiang
Liu, Zhanxiang
Zhang, Yuhong
[J]. ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (12): : 2428 - 2432
[8] Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization
Suzuki, Kana
Hattori, Yasunao
Kawamura, Atsushi
Makabe, Hidefumi
[J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2021, 85 (02) : 223 - 227
[9] Synthesis of a sulfur-bridged calixarene
Konig, B
Rodel, M
Dix, I
Jones, PG
[J]. JOURNAL OF CHEMICAL RESEARCH-S, 1997, (03): : 69 - &
[10] A new Pd-catalyzed cascade reaction for the synthesis of strained aromatic polycycles
Blond, Gaelle
Bour, Christophe
Salem, Bahaa
Suffert, Jean
[J]. ORGANIC LETTERS, 2008, 10 (06) : 1075 - 1078

← 1 2 3 4 5 →