Pd(II)-Catalyzed C-H Silylation of o-Alkynylanilines Initiated by an Aminopalladation To Access Disilylated 2-Phenyl-1H-indoles

被引:3
作者
Chen, Yan [1 ,2 ]
Zhu, Ling [1 ,2 ]
Tan, Xuliang [1 ,2 ]
Chen, Xiahong [1 ,2 ]
Deng, Guobo [1 ,2 ]
Liang, Yun [1 ,2 ]
Yang, Yuan [1 ,2 ]
机构
[1] Hunan Normal Univ, Natl & Local Joint Engn Lab New Petro Chem Mat & F, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ,Coll Chem & Chem Engn, Changsha 410081, Peoples R China
[2] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Peoples R China
基金
中国国家自然科学基金;
关键词
C; C-palladacycles; C-H silylation; o-alkynylanilines; aminopalladation; disilylated; 2-phenyl-1H-indoles; DIRECT INTERMOLECULAR SILYLATION; STEREOSELECTIVE-SYNTHESIS; ACTIVATION; GERMANYLATION; DIVERGENT; FUNCTIONALIZATION; PALLADACYCLES; VINYLSILANES; ALKENES; ALKYNES;
D O I
10.1002/adsc.202301119
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Herein a Pd(II)-catalyzed C-H silylation of o-alkynylanilines with hexamethyldisilane for the synthesis of disilylated 2-phenyl-1H-indoles is reported. In this reaction, o-alkynylanilines undergo an aminopalladation, C-H activation, and dealkylation sequence to form five-membered C,C-palladacycles, which then couple with hexamethyldisilane to construct one C-N bond and two C-Si bonds. This method provides an alternative strategy for C-H silylation.
引用
收藏
页码:183 / 187
页数:5
相关论文
共 77 条
[1]   A carboxylate-assisted amination/unactivated C(sp2)-H arylation reaction via a palladium/norbornene cooperative catalysis [J].
An, Yang ;
Zhang, Bo-Sheng ;
Zhang, Zhe ;
Liu, Ce ;
Gou, Xue-Ya ;
Ding, Ya-Nan ;
Liang, Yong-Min .
CHEMICAL COMMUNICATIONS, 2020, 56 (44) :5933-5936
[2]   C-H hetero-functionalization of arenes through palladacyclopentane-type intermediates [J].
Cao, Liming ;
Hua, Yu ;
Cheng, Hong-Gang ;
Zhou, Qianghui .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (14) :3883-3914
[3]   Poly(2,7-dibenzosilole): A blue light emitting polymer [J].
Chan, KL ;
McKiernan, MJ ;
Towns, CR ;
Holmes, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) :7662-7663
[4]   Palladium-Catalyzed Oxalyl Amide Directed Silylation and Germanylation of Amine Derivatives [J].
Chen, Changpeng ;
Guan, Mingyu ;
Zhang, Jingyu ;
Wen, Zhenkang ;
Zhao, Yingsheng .
ORGANIC LETTERS, 2015, 17 (15) :3646-3649
[5]   Palladium-catalyzed domino Heck-disilylation and Heck-monosilylation of alkene-tethered carbamoyl chlorides: synthesis of versatile silylated oxindoles [J].
Chen, Chen ;
Sun, Wan ;
Liu, Liying ;
Zhao, Jinghui ;
Huang, Yujie ;
Shi, Xiaonan ;
Ding, Jie ;
Jiao, Dequan ;
Zhu, Bolin .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (10) :2250-2255
[6]   Intermolecular C-H silylation through cascade carbopalladation and vinylic to aryl 1,4-palladium migration [J].
Cheng, Cang ;
Zhu, Qiongqiong ;
Zhang, Yanghui .
CHEMICAL COMMUNICATIONS, 2021, 57 (76) :9700-9703
[7]   Catalytic Silylation of Unactivated C-H Bonds [J].
Cheng, Chen ;
Hartwig, John F. .
CHEMICAL REVIEWS, 2015, 115 (17) :8946-8975
[8]   Experimental and Computational Studies on Remote γ-C(sp3)-H Silylation and Germanylation of Aliphatic Carboxamides [J].
Deb, Arghya ;
Singh, Sukriti ;
Seth, Kapileswar ;
Pimparkar, Sandeep ;
Bhaskararao, Bangaru ;
Guin, Srimanta ;
Sunoj, Raghavan B. ;
Maiti, Debabrata .
ACS CATALYSIS, 2017, 7 (12) :8171-8175
[9]   Domino C-N Bond Formation via a Palladacycle with Diaziridinone. An Approach to Indolo[3,2-b]indoles [J].
Debnath, Sudarshan ;
Liang, Lingli ;
Lu, Mei ;
Shi, Yian .
ORGANIC LETTERS, 2021, 23 (09) :3237-3242
[10]   Palladium(II)-Catalyzed Intramolecular Tandem Aminoalkylation via Divergent C(sp3) H Functionalization [J].
Du, Wei ;
Gu, Qiangshuai ;
Li, Zhongliang ;
Yang, Dan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (03) :1130-1135