Ru(II)-Catalyzed Decarbonylative Alkylation and Annulations of Benzaldehydes with Iodonium Ylides under Chelation Assistance

被引：27

作者：

Li, Xiang ^{[1
]}

Shen, Yang ^{[1
]}

Zhang, Guodong ^{[2
]}

Zheng, Xin ^{[1
]}

Zhao, Qing ^{[1
]}

Song, Zihe ^{[1
]}

机构：

[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China

[2] Yangzhou Univ, Coll Chem & Chem Engn, 180 Siwangting Rd, Yangzhou 225002, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 29期

基金：

中国国家自然科学基金;

关键词：

C-H ACTIVATION; DIVERGENT SYNTHESIS; INDOLE ALKALOIDS; FORMAL SYNTHESIS; SALICYLALDEHYDES; CONSTRUCTION; DIBENZOFURANS; ALDEHYDES; CHROMONES; ALKYNES;

D O I：

10.1021/acs.orglett.2c01843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Ru(II)-catalyzed decarbonylative alkylation and annulation of salicylaldehydes and 2-aminobenzaldehydes with iodonium ylides has been developed for the synthesis of dibenzo[b,d]furans and NH-free carbazolones. The reaction proceeds smoothly under mild conditions with a low catalyst loading and a broad substrate compatibility. Notably, hydroxy and free amino groups were demonstrated to be the effective directing groups, enabling the successful aldehyde C-H bond activation and subsequent decarbonylation and annulation under the inexpensive Ru(II) catalyst.

引用

页码：5281 / 5286

页数：6

共 61 条

[1] Cu-Catalyzed Reaction of 1,2-Dihalobenzenes with 1,3-Cyclohexanediones for the Synthesis of 3,4-Dihydrodibenzo[b,d]furan-1(2H)-ones
Aljaar, Nayyef
Malakar, Chandi C.
Conrad, Juergen
Strobel, Sabine
Schleid, Thomas
Beifuss, Uwe
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (18) : 7793 - 7803
[2] Ru(II)-Catalyzed C-H activation and annulation of salicylaldehydes with monosubstituted and disubstituted alkynes
Baruah, Swagata
Kaishap, Partha Pratim
Gogoi, Sanjib
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (88) : 13004 - 13007
[3] Construction of Diverse and Functionalized 2H-Chromenes by Organocatalytic Multicomponent Reactions
Cai, Hongyun
Xia, Likai
Lee, Yong Rok
Shim, Jae-Jin
Kim, Sung Hong
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5212 - 5220
[4] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
Cai, Libo
Zhu, Xiaoyi
Chen, Jiayi
Lin, Aijun
Yao, Hequan
[J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
[5] Achyrofuran, a new antihyperglycemic dibenzofuran from the South American medicinal plant Achyrocline satureioides
Carney, JR
Krenisky, JM
Williamson, RT
Luo, J
[J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (02): : 203 - 205
[6] MAKALUVAMINE-G, A CYTOTOXIC PIGMENT FROM AN INDONESIAN SPONGE HISTODERMELLA SP
CARNEY, JR
SCHEUER, PJ
KELLYBORGES, M
[J]. TETRAHEDRON, 1993, 49 (38) : 8483 - 8486
[7] Carotenuto A, 1998, EUR J ORG CHEM, V1998, P661, DOI 10.1002/(SICI)1099-0690(199804)1998:4<661::AID-EJOC661>3.0.CO
[8] 2-V
[9] Nucleophilicity Parameters of Stabilized Iodonium Ylides for Characterizing Their Synthetic Potential
Chelli, Saloua
Troshin, Konstantin
Mayer, Peter
Lakhdar, Sami
Ofial, Armin R.
Mayr, Herbert
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (32) : 10304 - 10313
[10] Cobalt(II)-tetraphenylporphyrin-catalysed carbene transfer from acceptor-acceptor iodonium ylides via N-enolate-carbene radicals
Epping, Roel F. J.
Hoeksma, Mees M.
Bobylev, Eduard O.
Mathew, Simon
de Bruin, Bas
[J]. NATURE CHEMISTRY, 2022, 14 (05) : 550 - +

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