OBSERVATION OF 2,7-DISUBSTITUTION IN PALLADIUM CATALYSED DIRECTED C-H ACTIVATION OF INDOLES

被引：7

作者：

Fanton, Guilia ^{[1
]}

Coles, Nicola M. ^{[1
]}

Cowley, Andrew R. ^{[1
]}

Flemming, Jonathan P. ^{[1
]}

Brown, John M. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

HETEROCYCLES | 2010年 / 80卷 / 02期

基金：

英国工程与自然科学研究理事会;

关键词：

Palladium (II); Alkenylation; Indole; Directing Group; X-Ray; FUNCTIONALIZATION; ALKENYLATION; OLEFINS;

D O I：

10.3987/COM-09-S(S)117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In previous work, controlled C-H activation and catalytic Heck reaction at the 2-position of indole was demonstrated. This was achieved by means of a N-(2-pyridylmethyl) directing group. In the course of extending the initial observations it was discovered that the corresponding N-(1-isoquinolylmethyl)indole derivative was prone to a further oxidative Heck reaction giving rise to a 2,7-disubstituted product, which was characterised by NMR and X-ray analysis. The parent pyridine showed no tendency for a second substitution reaction at the indole 7-position, but the related N-(2-quinolylmethyl) derivative did. In the case of the corresponding 6-methylphenanthridinyl derivative, a novel oxidative C-C cleavage reaction was observed.

引用

页码：895 / 901

页数：7

共 33 条

[1]

Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062

[2]

[Anonymous], 2004, ACS S SER

[3] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].