Pd-Catalyzed C-H Carbonylation of (Hetero)arenes with Formates and Intramolecular Dehydrogenative Coupling: A Shortcut to Indolo[3,2-c]coumarins

被引：49
作者：
Wu, Jie
Lan, Jingbo [1 ]
Guo, Siyuan
You, Jingsong
机构：
[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, Chengdu 610064, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 22期
关键词：
ARYL HALIDES; NATURAL-PRODUCTS; BOND ACTIVATION; CARBON-MONOXIDE; DERIVATIVES; HETEROARENES; NUCLEOPHILES; INHIBITORS; ARYLATION;
D O I：
10.1021/ol502749b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient protocol for the synthesis of (hetero)aryl carboxylic esters has been achieved by Pd-catalyzed CH carbonylation of (hetero)arenes with aryl formates. A relatively wide range of functional groups can be tolerated in this transformation, and the corresponding esters are obtained in good yields. On this basis, an intramolecular oxidative CH/CH coupling has been developed to prepare indolo[3,2-c]coumarins.
引用
收藏
页码：5862 / 5865
页数：4
相关论文
共 44 条
[1]   Palladium-Catalyzed Carbonylation-A Reaction Come of Age [J].
Barnard, Christopher F. J. .
ORGANOMETALLICS, 2008, 27 (21) :5402-5422
[2]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[3]   C-H Activation: A Complementary Tool in the Total Synthesis of Complex Natural Products [J].
Chen, David Y. -K. ;
Youn, So Won .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (31) :9452-9474
[4]   In-silico fragment-based identification of novel angiogenesis inhibitors [J].
Dakshanamurthy, Sivanesan ;
Kim, Min ;
Brown, Milton L. ;
Byers, Stephen W. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (16) :4551-4556
[5]   A General Method for Copper-Catalyzed Arene Cross-Dimerization [J].
Do, Hien-Quang ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (34) :13577-13586
[6]   Rhodium or Ruthenium-Catalyzed Oxidative C?H/C?H Cross-Coupling: Direct Access to Extended p-Conjugated Systems [J].
Dong, Jiaxing ;
Long, Zhen ;
Song, Feijie ;
Wu, Ningjie ;
Guo, Qiang ;
Lan, Jingbo ;
You, Jingsong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :580-584
[7]   Palladium-catalyzed esterification of aryl halides using aryl formates without the use of external carbon monoxide [J].
Fujihara, Tetsuaki ;
Hosoki, Tomoya ;
Katafuchi, Yuko ;
Iwai, Tomohiro ;
Terao, Jun ;
Tsuji, Yasushi .
CHEMICAL COMMUNICATIONS, 2012, 48 (64) :8012-8014
[8]   GR113808 - A NOVEL, SELECTIVE ANTAGONIST WITH HIGH-AFFINITY AT THE 5-HT4 RECEPTOR [J].
GALE, JD ;
GROSSMAN, CJ ;
WHITEHEAD, JWF ;
OXFORD, AW ;
BUNCE, KT ;
HUMPHREY, PPA .
BRITISH JOURNAL OF PHARMACOLOGY, 1994, 111 (01) :332-338
[9]   Pd-catalyzed double C-H bond activation of diaryl ketones for the synthesis of fluorenones [J].
Gandeepan, Parthasarathy ;
Hung, Chen-Hsun ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2012, 48 (75) :9379-9381
[10]   Dye-sensitized nanocrystalline TiO2 solar cells based on novel coumarin dyes [J].
Hara, K ;
Tachibana, Y ;
Ohga, Y ;
Shinpo, A ;
Suga, S ;
Sayama, K ;
Sugihara, H ;
Arakawa, H .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2003, 77 (01) :89-103
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