Carbon-nitrogen bond-forming reactions of palladacycles with hypervalent iodine reagents

被引：121

作者：

Dick, Allison R. ^{[1
]}

Remy, Matthew S. ^{[1
]}

Kampf, Jeff W. ^{[1
]}

Sanford, Melanie S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANOMETALLICS | 2007年 / 26卷 / 06期

关键词：

D O I：

10.1021/om061052l

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium(II) complexes containing bidentate cyclometalated C similar to N chelating ligands are shown to react with PhINTs at room temperature to insert "NTs" into the Pd-C bond. This "NTs" insertion reaction has been applied to palladacyclic complexes of azobenzene, benzo[h]quinoline, and 8-ethylquinoline. The newly aminated organic ligands can be liberated from the metal center by protonolysis with trifluoroacetic acid or HCl.

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页码：1365 / 1370

页数：6

相关论文

共 56 条

[1] RIGID 5-MEMBERED AND 6-MEMBERED C,N,N'-BOUND ARYL, BENZYL, AND ALKYL ORGANOPALLADIUM COMPLEXES - SP(2) VS SP(3) C-H ACTIVATION DURING CYCLOPALLADATION AND PALLADIUM(IV) INTERMEDIATES IN OXIDATIVE ADDITION-REACTIONS WITH DIHALOGENS AND ALKYL-HALIDES [J].

ALSTERS, PL ;

ENGEL, PF ;

HOGERHEIDE, MP ;

COPIJN, M ;

SPEK, AL ;

VANKOTEN, G .

ORGANOMETALLICS, 1993, 12 (05) :1831-1844

[2] OXYGENATION OF CYCLOPALLADATED N,N-DIMETHYLBENZYLAMINE COMPLEXES BY INORGANIC AND ORGANIC PEROXIDES - OXYGEN INSERTION INTO THE PALLADIUM-CARBON BOND [J].

ALSTERS, PL ;

TEUNISSEN, HT ;

BOERSMA, J ;

SPEK, AL ;

VANKOTEN, G .

ORGANOMETALLICS, 1993, 12 (11) :4691-4696

[3] OXYGEN INSERTION INTO PALLADIUM-ARENE BONDS BY IODOSYLBENZENE [J].

BHAWMICK, R ;

BISWAS, H ;

BANDYOPADHYAY, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 498 (01) :81-83

[4] INTRAMOLECULAR NITRENE C-H INSERTIONS MEDIATED BY TRANSITION-METAL COMPLEXES AS NITROGEN ANALOGS OF CYTOCHROME-P-450 REACTIONS [J].

BRESLOW, R ;

GELLMAN, SH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6728-6729

[5]

Bugarcic Z.D., 2002, DALTON T, P951

[6] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[7] REACTIVITY OF COORDINATED LIGANDS .15. FORMATION OF COMPLEXES CONTAINING GROUP V DONOR ATOMS AND METAL-CARBON SIGMA BONDS [J].

COCKBURN, BN ;

HOWE, DV ;

KEATING, T ;

JOHNSON, BFG ;

LEWIS, J .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1973, (04) :404-410

[8] FORMATION OF COVALENT BONDS FROM PLATINUM OR PALLADIUM TO CARBON BY DIRECT SUBSTITUTION [J].

COPE, AC ;

SIEKMAN, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3272-&

[9] Anilide ortho-arylation by using C-H activation methodology [J].

Daugulis, O ;

Zaitsev, VG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4046-4048

[10] Room temperature palladium-catalyzed 2-arylation of indoles [J].

Deprez, NR ;

Kalyani, D ;

Krause, A ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4972-4973

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