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

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