Versatile Synthesis of Polyfunctionalized Carbazoles from (3-Iodoindol-2-yl)butynols via a Gold-Catalyzed Intramolecular Iodine-Transfer Reaction

被引：48

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Alonso, Jose M. ^{[1
]}

Busto, Eduardo ^{[1
]}

Fernandez, Israel ^{[3
]}

Pilar Ruiz, M. ^{[1
]}

Xiaokaiti, Gulinigaer ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Ciencias Quim, Grp Lactamas & Heterociclos Bioact, Dept Quim Organ 1,Unidad Asociada,CSIC, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[3] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

ACS CATALYSIS | 2015年 / 5卷 / 06期

关键词：

alkynes; cyclization; density functional calculations; gold; iodine; ORGANIC-SYNTHESIS; CYCLIZATION; CARBOIODINATION; ENTRY;

D O I：

10.1021/acscatal.5b00471

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The controlled gold-catalyzed preparation of 3-iodo 2,4,6-trisubstituted 9H-carbazoles has been developed by starting from (3-iodoindo1-2-yl)butynols. These results could be explained through an initial 6-endo-dig alkyne carbocydization by chemo- and regiospecific attack of the C3-indole position at the external alkyne R2 carbon followed by a stepwise 1,3-iodine transfer and dehydration. This reaction outcome for the gold-catalyzed transformation of (3-iodoindo1-2-yl)alkynols sharply contrasts with that observed for conventional metal-catalyzed processes of iodoarenes, because iodine transfer is feasible. This selective reaction has been studied experimentally; additionally, its mechanism has been investigated by means of density functional theory calculations.

引用

页码：3417 / 3421

页数：5

共 6 条

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Wu, Yufeng
Zhu, Lei
Yu, Yinghua
Luo, Xuesong
Huang, Xueliang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (22): : 11407 - 11416
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Fabrizi, Giancarlo
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Fan, Ling
Ren, Tianbing
Zheng, Chunyang
Tao, Qing
Wu, Anxin
She, Nengfang
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) : 8877 - 8883
[4] Gold-Catalyzed Synthesis of 3-Pyrrolidinones and Nitrones from N-Sulfonyl Hydroxylamines via Oxygen-Transfer Redox and 1,3-Sulfonyl Migration
Yeom, Hyun-Suk
So, Eunsu
Shin, Seunghoon
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (06) : 1764 - 1767
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Kumari, A. Leela Siva
Swamy, K. C. Kumara
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08): : 4084 - 4096
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Yu, Xiao
Liu, Hong-Yan
Liu, Yi
Zhao, Jin-Bo
Zhang, Peng-Fei
Xia, Cheng-Cai
Li, Fu-Rong
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (31) : 6307 - 6311

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