Ruthenium(ii)-catalyzed chemoselective deacylative annulation of 1,3-diones with sulfoxonium ylides via C-C bond activation

被引:55
作者
Wen, Si [1 ]
Lv, Weiwei [1 ]
Ba, Dan [1 ]
Liu, Jing [1 ]
Cheng, Guolin [1 ]
机构
[1] Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Fujian, Peoples R China
关键词
CARBON-CARBON BOND; REGIOSPECIFIC SYNTHESIS; POLYSUBSTITUTED FURANS; ARYL KETONES; H BONDS; CLEAVAGE; CATALYSIS; INSERTION; PYRROLES; FUNCTIONALIZATION;
D O I
10.1039/c9sc03245b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first successful example of deacylative annulation of 1,3-diones with sulfoxonium ylides was achieved through Ru(ii)-catalyzed C-C bond activation. The excellent chemoselectivity and broad substrate scope render this method a practical and versatile approach for the preparation of (hetero)aryl and alkenyl substituted furans, which are valuable units in many biologically active compounds and functional materials. A preliminary mechanistic study reveals that this process involves a deacylative alpha-ruthenation to generate key alkyl Ru(ii) intermediates with the release of a benzoic acid fragment.
引用
收藏
页码:9104 / 9108
页数:5
相关论文
共 64 条
[21]   Copper Catalyzed Arylation/C-C Bond Activation: An Approach toward α-Aryl Ketones [J].
He, Chuan ;
Guo, Sheng ;
Huang, Li ;
Lei, Aiwen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8273-+
[22]   From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air [J].
Huang, Xiaoqiang ;
Li, Xinyao ;
Zou, Miancheng ;
Song, Song ;
Tang, Conghui ;
Yuan, Yizhi ;
Jiao, Ning .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (42) :14858-14865
[23]   Cp*Co(III)-Catalyzed C-H Acylmethylation of Arenes by Employing Sulfoxonium Ylides as Carbene Precursors [J].
Ji, Shuying ;
Yan, Kelu ;
Li, Bin ;
Wang, Baiquan .
ORGANIC LETTERS, 2018, 20 (18) :5981-5984
[24]   Transition metal-catalyzed carbon-carbon bond activation [J].
Jun, CH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :610-618
[25]   Metal-Organic Cooperative Catalysis in C-H and C-C Bond Activation [J].
Kim, Dong-Su ;
Park, Woo-Jin ;
Jun, Chul-Ho .
CHEMICAL REVIEWS, 2017, 117 (13) :8977-9015
[26]   Syntheses of polysubstituted furans: recent developments [J].
Kirsch, SF .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2076-2080
[27]   Gold-Catalyzed Carbene Transfer to Alkynes: Access to 2,4-Disubstituted Furans [J].
Kramer, Soren ;
Skrydstrup, Troels .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (19) :4681-4684
[28]   Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions [J].
Lee, Hyejeong ;
Yi, Yeonhui ;
Jun, Chul-Ho .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) :3485-3490
[29]   Extrusion of CO from Aryl Ketones: Rhodium(I)-Catalyzed C?C Bond Cleavage Directed by a Pyridine Group [J].
Lei, Zhi-Quan ;
Li, Hu ;
Li, Yang ;
Zhang, Xi-Sha ;
Chen, Kang ;
Wang, Xin ;
Sun, Jian ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (11) :2690-2694
[30]   Silver-Catalyzed Oxidative C(sp3)-P Bond Formation through C-C and P-H Bond Cleavage [J].
Li, Lili ;
Huang, Wenbin ;
Chen, Lijin ;
Dong, Jiaxing ;
Ma, Xuebing ;
Peng, Yungui .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) :10539-10544