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

来源：

CHEMICAL SCIENCE | 2019年 / 10卷 / 39期

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

页码：9104 / 9108

页数：5

共 64 条

[1] Regioselective Synthesis of Fused Furans by Decarboxylative Annulation of α,β-Alkenyl Carboxylic Acid with Cyclic Ketone: Synthesis of Di-Heteroaryl Derivatives [J].

Agasti, Soumitra ;

Pal, Tapas ;

Achar, Tapas Kumar ;

Maiti, Siddhartha ;

Pal, Debasis ;

Mandal, Smita ;

Daud, Kishan ;

Lahiri, Goutam Kumar ;

Maiti, Debabrata .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) :11039-11043

[2] Dual Oxidation State Tandem Catalysis in the Palladium-Catalyzed Isomerization of Alkynyl Epoxides to Furans [J].

Arroniz, Carlos ;

Chaubet, Guilhem ;

Anderson, Edward A. .

ACS CATALYSIS, 2018, 8 (09) :8290-8295

[3] Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds [J].

Barday, Manuel ;

Janot, Christopher ;

Halcovitch, Nathan R. ;

Muir, James ;

Aissa, Christophe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13117-13121

[4]

Boto A, 2011, HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS, P99

[5] Developments in furan syntheses [J].

Brown, RCD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (06) :850-852

[6] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].

Chen, Feng ;

Wang, Teng ;

Jiao, Ning .

CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661

[7] "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation [J].

Chen, Peng-hao ;

Billett, Brent A. ;

Tsukamoto, Tatsuhiro ;

Dong, Guangbin .

ACS CATALYSIS, 2017, 7 (02) :1340-1360

[8] Base-promoted ring-closing carbonyl-allene metathesis for the synthesis of 2,4-disubstituted pyrroles [J].

Cheng, Guolin ;

Lv, Weiwei ;

Xue, Lulu .

GREEN CHEMISTRY, 2018, 20 (19) :4414-4417

[9] Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C-C bond cleavage [J].

Cheng, Guolin ;

Lv, Weiwei ;

Kuai, Changsheng ;

Wen, Si ;

Xiao, Shangyun .

CHEMICAL COMMUNICATIONS, 2018, 54 (14) :1726-1729

[10] A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles [J].

Cheng, Guolin ;

Zeng, Xiaobao ;

Shen, Jinhai ;

Wang, Xuesong ;

Cui, Xiuling .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) :13265-13268

← 1 2 3 4 5 6 7 →