The scope and limitations of deuteration mediated by Crabtree's catalyst

被引：90

作者：

Ellames, GJ ^{[1
]}

Gibson, JS ^{[1
]}

Herbert, JM ^{[1
]}

McNeill, AH ^{[1
]}

机构：

[1] Sanofi Synthelabo, Isotope Chem & Metabolite Synth Dept, Alnwick NE66 2JH, Northd, England

来源：

TETRAHEDRON | 2001年 / 57卷 / 46期

关键词：

iridium complexes; deuterium exchange; isotope exchange;

D O I：

10.1016/S0040-4020(01)00945-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Exchange of protons for deuterons mediated by Crabtree's catalyst, 1, is directed efficiently by a functional group containing an sp(2)-hybridised nitrogen or oxygen atom; more electron-rich substrates are, in general, deuterated more efficiently. The electronic effects of substituents in the arene ring are critical only where the directing group is poor, in which case exchange is generally promoted by electron donating substituents, but the exchange is impeded by bulky meta-substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9487 / 9497

页数：11

共 43 条

[1] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ARYLBORONIC ACIDS WITH PI-DEFICIENT HETEROARYL CHLORIDES [J].

ALI, NM ;

MCKILLOP, A ;

MITCHELL, MB ;

REBELO, RA ;

WALLBANK, PJ .

TETRAHEDRON, 1992, 48 (37) :8117-8126

[2]

Bauer W, 1998, EUR J INORG CHEM, P485

[3] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES [J].

BEADLE, JR ;

KORZENIOWSKI, SH ;

ROSENBERG, DE ;

GARCIASLANGA, BJ ;

GOKEL, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1594-1603

[4] THE GEOMETRY OF DISPLACEMENTS AT NONSTEREOGENIC ATOMS - THE FORMAL DISPLACEMENT OF ALKOXIDE FROM ALKOXYAMINES BY ORGANOLITHIUM REAGENTS [J].

BEAK, P ;

BASHA, A ;

KOKKO, B ;

LOO, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6016-6023

[5]

BEDFORD RB, 1995, CHEM INDUST, V62, P181

[6] Preparation and NMR spectroscopic studies of the glucuronides of Irbesartan [J].

Byard, SJ ;

Herbert, JM .

TETRAHEDRON, 1999, 55 (18) :5931-5936

[7]

Chen W, 1997, J LABELLED COMPD RAD, V39, P291, DOI 10.1002/(SICI)1099-1344(199704)39:4<291::AID-JLCR973>3.0.CO

[8]

2-K

[9] ARENE AND CYCLOHEXADIENYL COMPLEXES AS INTERMEDIATES IN THE SELECTIVE CATALYTIC DEHYDROGENATION OF CYCLOHEXENES TO ARENES [J].

CRABTREE, RH ;

PARNELL, CP .

ORGANOMETALLICS, 1985, 4 (03) :519-523

[10] A NEW EFFICIENT SYNTHESIS OF ETHYL BETA-CARBOLINE-3-CARBOXYLATE (BETA-CCE) AND METHYL 4-METHYL-BETA-CARBOLINE-3-CARBOXYLATE (4-METHYL-BETA-CCM) STARTING FROM INDOLE-2 CARBOXALDEHYDE [J].

DEKHANE, M ;

DODD, RH .

TETRAHEDRON, 1994, 50 (21) :6299-6306

← 1 2 3 4 5 →