The photodecarboxylative addition of carboxylates to phthalimides:: Scope and limitations

被引：33

作者：

Oelgemöller, M ^{[1
]}

Cygon, P ^{[1
]}

Lex, J ^{[1
]}

Griesbeck, AG ^{[1
]}

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

来源：

HETEROCYCLES | 2003年 / 59卷 / 02期

关键词：

D O I：

10.3987/COM-02-S77

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular photoinduced decarboxylative additions of a series of alkylcarboxylates to N-substituted phthalimides gave the corresponding hydroxy-plithalimidines in moderate to high yields of 39-89%. The potassium salt of 1-adamantanecarboxylic acid predominately underwent simple decarboxylation when irradiated in the presence of N-methylphthalimide. In case of phthalimides carrying suitable leaving groups within the N-side chain, decarboxylation, retro-Aldol cleavage or decarbonylation preceded the intermolecular addition step.

引用

页码：669 / 684

页数：16

共 35 条

[1] Environment-friendly organic synthesis. The photochemical approach [J].

Albini, A ;

Fagnoni, M ;

Mella, M .

PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1321-1326

[2]

[Anonymous], SYNTHETIC ORGANIC PH

[3]

[Anonymous], ORG PHOTOCHEM

[4] Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides [J].

Farcas, S ;

Namy, JL .

TETRAHEDRON LETTERS, 2001, 42 (05) :879-881

[5] PHOTOCHEMICAL-REACTION OF PHTHALIMIDES AND DICYANOPHTHALIMIDES WITH BENZYLIC DONORS [J].

FRECCERO, M ;

FASANI, E ;

ALBINI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1740-1745

[6]

Griesbeck AG, 2001, EUR J ORG CHEM, V2001, P1831, DOI 10.1002/1099-0690(200105)2001:10<1831::AID-EJOC1831>3.0.CO

[7]

2-7

[8] Sustainable photochemistry: solvent-free singlet oxygen-photooxygenation of organic substrates embedded in porphyrin-loaded polystyrene beads [J].

Griesbeck, AG ;

Bartoschek, A .

CHEMICAL COMMUNICATIONS, 2002, (15) :1594-1595

[9] Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of omega-phthalimidoalkanoates [J].

Griesbeck, AG ;

Henz, A ;

Kramer, W ;

Lex, J ;

Nerowski, F ;

Oelgemoller, M ;

Peters, K ;

Peters, EM .

HELVETICA CHIMICA ACTA, 1997, 80 (03) :912-933

[10]

Griesbeck AG, 1999, SYNLETT, P492

← 1 2 3 4 →