Novel gallium-mediated C3-allylation of indoles and pyrroles in aqueous media promoted by Bu4NBr

被引：30

作者：

Prajapati, Dipak ^{[1
]}

Gohain, Mukut ^{[1
]}

Gogoi, Baikuntha J. ^{[1
]}

机构：

[1] Reg Res Lab, Med Chem Div, Jorhat 785006, Assam, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 21期

关键词：

gallium; cadmium; aqueous media;

D O I：

10.1016/j.tetlet.2006.03.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient protocol for the coupling of indoles and pyrroles with allyl halides such as allyl bromide, crotyl bromide and propargyl bromide in the presence of gallium metal in a Bu4NBr-DMF-H2O system has been developed. The reaction is equally effective when cadmium is used in lieu of gallium and the corresponding 3-allyl indoles and 3-allyl pyrroles were obtained in almost comparable yields. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3535 / 3539

页数：5

共 17 条

[1] Pd(II)/Bu4NBr/DMSO Catalytic System for Practical Synthesis of Indoles and Pyrroles from Imines through Aerobic Dehydrogenative Cyclization
Tan, Wei Wen
Hou, Xiaoya
Yoshikai, Naohiko
SYNTHESIS-STUTTGART, 2014, 46 (20): : 2727 - 2733
[2] Oxidative Bromination Reactions in Aqueous Media by Using Bu4NBr/TFA/H2O2 System
Moriuchi, Toshiyuki
Fukui, Yasuhiro
Sakuramoto, Takashi
Hirao, Toshikazu
CHEMISTRY LETTERS, 2017, 46 (12) : 1708 - 1710
[3] B(3,4,5-F3H2C6)3 Lewis acid-catalysed C3-allylation of indoles
Alotaibi, Nusaybah
Babaahmadi, Rasool
Pramanik, Milan
Kaehler, Tanja
Dasgupta, Ayan
Richards, Emma
Ariafard, Alireza
Wirth, Thomas
Melen, Rebecca L. L.
DALTON TRANSACTIONS, 2023, 52 (16) : 5039 - 5043
[4] PIDA/Bu4NBr/KOH-Oxidized Direct α-Acetoxylation of sp3 C-H Bonds Adjacent to Carbonyl
Liu, Wei-Bing
Chen, Cui
Zhang, Qing
Zhu, Zhi-Bo
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (06): : 1823 - 1824
[5] CONDUCTANCE-VISCOSITY STUDIES ON SOME MODERATELY CONCENTRATED NON-AQUEOUS ELECTROLYTE SOLUTIONS FROM -50 DEGREES TO 125 DEGREES C .2. SOLUTIONS OF PR4NBR, BU4NBR, AND BU4NL IN PROPYLENE CARBONATE
CASTEEL, JF
ANGEL, JR
MCNEELEY, HB
SEARS, PG
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1975, 122 (03) : 319 - 324
[6] YTTERBIUM TRIFLUOROMETHANESULFONATE [YB(OTF)3] PROMOTED INDIUM MEDIATED ALLYLATION REACTIONS OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA
WANG, RB
LIM, CM
TAN, CH
LIM, BK
SIM, KY
LOH, TP
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 1825 - 1828
[7] CHEMICAL-SHIFTS OF H-1, BR-79, O-17,C-13, AND N-14 IN AQUEOUS-SOLUTION OF BU4NBR
KOPPEL, IA
EIBER, VA
KOPPEL, JB
PEHK, TJ
ORGANIC REACTIVITY, 1988, 25 (01): : 58 - 76
[8] A novel synthesis of N-methyl-N-aryl carbamates from aromatic amines and dimethyl carbonate catalyzed by K2CO3/Bu4NBr
Shen, ZL
Jiang, XZ
CHINESE CHEMICAL LETTERS, 2004, 15 (08) : 889 - 891
[9] A Novel Synthesis of N-Methyl-N-aryl Carbamates from Aromatic Amines and Dimethyl Carbonate Catalyzed by K2CO3/Bu4NBr
Zhen Lu SHEN
Chinese Chemical Letters, 2004, (08) : 889 - 891
[10] Selectfluor-Bu4NI-Mediated C(sp3)-H Oxidation in Aqueous Media: Synthesis of 2-Isoxazolines from Oximes
Shi, Di
Qin, Hai-Tao
Zhu, Chen
Liu, Feng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (23) : 5084 - 5088

← 1 2 →