Pyrrole synthesis catalyzed by AgOTf or cationic Au(I) complexes

被引：132

作者：

Harrison, Tyler J. ^{[1
]}

Kozak, Jennifer A. ^{[1
]}

Corbella-Pane, Montserrat ^{[1
]}

Dake, Gregory R. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 12期

关键词：

D O I：

10.1021/jo060382c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Either silver trifluoromethanesulfonate or a mixture of gold( I) chloride, silver trifluoromethanesulfonate, and triphenylphosphine catalyze the formation of pyrroles from substituted beta-alkynyl ketones and amines. The reactions proceed by using 5 mol % of catalyst with yields of isolated pyrroles ranging from 13% to 92%. Sixteen examples are used to compare the effectiveness of each catalyst.

引用

页码：4525 / 4529

页数：5

共 74 条

[31] An efficient acid-catalysed 5-endo-dig cyclisation method for pyrrole synthesis [J].

Knight, DW ;

Sharland, CM .

SYNLETT, 2003, (14) :2258-2260

[32] Novel three-step synthesis of (-(+)over-bar)-harmicine [J].

Knölker, HJ ;

Agarwal, S .

SYNLETT, 2004, (10) :1767-1768

[33] Addition of heterocycles to electron deficient olefins and alkynes catalyzed by gold(III) [J].

Li, ZG ;

Shi, ZJ ;

He, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (23) :5049-5054

[34] Catalaytic isomerization of 1,5-enynes to bicyclo [3.1.0]hexenes [J].

Luzung, MR ;

Markham, JP ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10858-10859

[35] STEREOSELECTIVE SYNTHESIS OF 2,5-DIHYDROFURANS BY SEQUENTIAL SN2' CLEAVAGE OF ALKYNYLOXIRANES AND AG+-CATALYZED CYCLIZATION OF THE ALLENYLCARBINOL PRODUCTS [J].

MARSHALL, JA ;

PINNEY, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7180-7184

[36] SYNTHESIS OF FURANS BY S(N)2' CYCLIZATION OF GAMMA-ALKYNYL ALLYLIC ALCOHOL DERIVATIVES [J].

MARSHALL, JA ;

BENNETT, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) :6110-6113

[37] SYNTHESIS OF FURANS BY AG(I)-PROMOTED CYCLIZATION OF ALLENYL KETONES AND ALDEHYDES [J].

MARSHALL, JA ;

WANG, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :960-969

[38] OBSERVATIONS REGARDING THE AG(I)-CATALYZED CONVERSION OF ALLENONES TO FURANS [J].

MARSHALL, JA ;

BARTLEY, GS .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7169-7171

[39] SYNTHESIS OF FURANS AND 2,5-DIHYDROFURANS BY AG(I)-CATALYZED ISOMERIZATION OF ALLENONES, ALKYNYL ALLYLIC ALCOHOLS, AND ALLENYLCARBINOLS [J].

MARSHALL, JA ;

SEHON, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5966-5968

[40]

MASQUELIN T, 1995, SYNTHESIS-STUTTGART, P276

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