A Fast Track to Ind les and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides

被引：24

作者：

Jafarpour, Farnaz ^{[1
]}

Ghasemi, Mehran ^{[2
]}

Mohaghegh, Farid ^{[1
]}

Asgari, Sara ^{[1
]}

Habibi, Azizollah ^{[2
]}

机构：

[1] Univ Tehran, Coll Sci, Sch Chem, Tehran 141556455, Iran

[2] Kharazmi Univ, Fac Chem, 43 Mofateh St,Enghelab Ave, Tehran 1571914911, Iran

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 24期

关键词：

C-H ACTIVATION; PALLADIUM-CATALYZED REACTION; ONE-STEP SYNTHESIS; EFFICIENT SYNTHESIS; INTERNAL ALKYNES; N BOND; 1,4-PALLADIUM MIGRATION; OXIDATIVE CYCLIZATION; CASCADE REACTION; DOMINO REACTION;

D O I：

10.1021/acs.orglett.9b04202

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A complementary site selective ortho- vs ipsoamination of aryl halides using non-electrophilic amine sources for construction of indole scaffolds is reported. A palladium-catalyzed alkyne insertion/C H activation/palladacycle amination via merger of three easily diversified components including iodoarenes, alkynes, and amines delivers indoles with different substitution patterns even in gram scales. By employing ortho-bromoanilines, a consecutive annulative pi-extension of indoles proceeds to construct indolo[1,2-f]phenanthridine scaffolds via four C-C and C-N bond formations in one pot.

引用

页码：10143 / 10148

页数：6

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