Palladium-Catalyzed C( sp3)- H Activation: A Facile Method for the Synthesis of 3,4-Dihydroquinolinone Derivatives**

被引：87

作者：

Yan, Jia-Xuan ^{[1
,2
]}

Li, Hu ^{[1
,2
]}

Liu, Xiang-Wei ^{[1
,2
]}

Shi, Jiang-Ling ^{[1
,2
]}

Wang, Xin ^{[1
,2
]}

Shi, Zhang-Jie ^{[1
,2
,3
]}

机构：

[1] Peking Univ, PKU Green Chem Ctr, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China

[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China

[3] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 19期

关键词：

CH activation; dihydroquinolinones; palladacycles; palladium; synthetic methods; INTRAMOLECULAR ALKANE ARYLATION; PROTON-ABSTRACTION MECHANISM; BOND ACTIVATION; UNACTIVATED C(SP(3))-H; EFFICIENT SYNTHESIS; DIRECTING GROUP; FUNCTIONALIZATION; LIGAND; ACID; (HETERO)ARENES;

D O I：

10.1002/anie.201402562

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

3,4-Dihydroquinolinones were synthesized by the palladium-catalyzed, oxidative-addition-initiated activation and arylation of inert C(sp(3))H bonds. Pd(OAc)(2) and P(o-tol)(3) were used as the catalyst and ligand, respectively, to improve the efficiency of the reaction. A further advantage of this reaction is that it could be performed in air. A relatively rare seven-membered palladacycle was proposed as a key intermediate of the catalytic cycle.

引用

页码：4945 / 4949

页数：5

共 50 条

[1] Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp3)-H Activation
Wu, Zhuo
Ma, Ding
Zhou, Bo
Ji, Xiaoming
Ma, Xiaotian
Wang, Xiaoling
Zhang, Yanghui
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (40) : 12288 - 12291
[2] Palladium-catalyzed silyl C(sp3)-H bond activation
Liang, Yun
Geng, Weizhi
Wei, Junnian
Ouyang, Kunbing
Xi, Zhenfeng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (08) : 1537 - 1542
[3] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
Wei, Wan-Xu
Czajkowski, Mateusz
Kuang, Yangjin
Nguyen, Tu-Anh V.
Qin, Bo
Tomanik, Martin
ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546
[4] Synthesis of Amides and Esters by Palladium(0)-Catalyzed Carbonylative C(sp3)-H Activation
Carny, Tomas
Rocaboy, Ronan
Clemenceau, Antonin
Baudoin, Olivier
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (43) : 18980 - 18984
[5] Palladium-Catalyzed Domino Mizoroki-Heck/Intermolecular C(sp3)-H Activation Sequence: An Approach to the Formation of C(sp3)-C(sp3) Bonds
Wang, Wei
Zhou, Rong
Jiang, Zhi-Jie
Wang, Xin
Fu, Hai-Yan
Zheng, Xue-Li
Chen, Hua
Li, Rui-Xiang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (12) : 2579 - 2584
[6] Synergistic Palladium-Catalyzed C(sp3)?H Activation/C(sp3)?O Bond Formation: A Direct, Step-Economical Route to Benzolactones
Novak, Petr
Correa, Arkaitz
Gallardo-Donaire, Joan
Martin, Ruben
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) : 12236 - 12239
[7] Palladium-Catalyzed Intermolecular C(sp3)-H Amidation
Iglesias, Alvaro
Alvarez, Rosana
de Lera, Angel R.
Muniz, Kilian
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) : 2225 - 2228
[8] Palladium-Catalyzed Remote C(sp3)-H Arylation of 3-Pinanamine
Cui, Wei
Chen, Shengwei
Wu, Jia-Qiang
Zhao, Xin
Hu, Wenhui
Wang, Honggen
ORGANIC LETTERS, 2014, 16 (16) : 4288 - 4291
[9] Palladium-Catalyzed Amidation by Chemoselective C(sp3)?H Activation: Concise Route to Oxindoles Using a Carbamoyl Chloride Precursor
Tsukano, Chihiro
Okuno, Masataka
Takemoto, Yoshiji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (11) : 2763 - 2766
[10] Palladium-Catalyzed Through-Space C(sp3)-H and C(sp2)-H Bond Activation by 1,4-Palladium Migration: Efficient Synthesis of [3,4]-Fused Oxindoles
Piou, Tiffany
Bunescu, Ala
Wang, Qian
Neuville, Luc
Zhu, Jieping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (47) : 12385 - 12389

← 1 2 3 4 5 →