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Photocatalytic Coupling Reactions of Halobenzenes With an Electron Withdrawing Group(PDF)

《南京师大学报(自然科学版)》[ISSN:1001-4616/CN:32-1239/N]

Issue:
2014年02期
Page:
75-
Research Field:
化学
Publishing date:

Info

Title:
Photocatalytic Coupling Reactions of Halobenzenes With an Electron Withdrawing Group
Author(s):
Yu Yili1Tang Jian12Ying Yeqi1Huang Mengmeng1Cheng Jie1Shen Xiangru1Shen Yongmiao1
(1. School of Chemistry and Chemical Engineering,Shaoxing University,Shaoxing 312000,China) (2. School of Chemistry and Materials Science,Nanjing Normal University,Nanjing 210023,China)
Keywords:
electron withdrawing grouphalobenzenephotocatalyticcoupling reaction
PACS:
O625. 21
DOI:
-
Abstract:
A series of biphenyl derivatives were synthesized by photocatalytic reactions of benzene derivatives(benzene, toluene,1,4-dimethylbenzene, oxydibenzene) with halobenzene which contains an electron withdrawing group ( Ester group,Acyl group). The optimal conditions for this dehydrohalogenative coupling reaction were determined and the influence of substituents on the yields were also discussed.

References:

[1]Chang J B,Reiner J,Xie J X. Progress on the chemistry of dibenzocyclooctadiene lignans[J]. Chem Rev,2005,105:4581-4609.
[2] Chen X F,Ke H H,Chen Y,et al. Cross-coupling of diarylborinic acids and anhydrides with arylhalides catalyzed by a phosphite/ N-heterocyclic carbene cosupported palladium catalyst system[J]. J Org Chem,2012,77:7572-7578.
[3] Liu C,Rao X F,Song X L,et al. Palladium-catalyzed ligand-free and aqueous Suzuki reaction for the construction of(hetero)aryl-substituted triphenylamine derivatives[J]. RSC Adv,2013,3(2):526-531.
[4] Li B J,Qin X R,You J S,et al. Direct arylation of phenanthroline derivatives via oxidative C—H/ C—H cross-coupling:synthesis and discovery of excellent ligands[J]. Org Biomol Chem,2013,11(8):1290-1293.
[5] Protti S,Fagnoni M,Mella M,et al. Aryl cations from aromatic halides photogeneration and reactivity of 4-Hydroxy(methoxy)phenyl cation[J]. J Org Chem,2004,69:3 465-3 473.
[6] Fagnoni M,Albini A. Arylation reactions:the photo-SN1 path via phenyl cation as an alternative to metal catalysis[ J]. Acc Chem Res,2005,38:713-721.
[7] Albini A,Dichiarante V. The‘belle époque’of photochemistry[J]. Photochem Photobiol Sci,2009(8):248-254.
[8] Fagnoni M,Daniele Dondi D,Ravelli D,et al. Photocatalysis for the formation of the C—C bond[J]. Chem Rev,2007,107:2 725-2 756.
[9] Protti S,Fagnoni M,Albini A. Metal-free cross-coupling reactions of aryl sulfonates and phosphates through photoheterolysis of aryl-oxygen bonds[J]. Angew Chem Int Ed,2005,44:5 675-5 678.
[10] Metallinos C,Barrett F B,Chaytor J L,et al. A benzimidazole-based N-Heterocyclic carbene derived from 1,10-Phenanthroline[J]. Org Lett,2004,6(20):3 641-3 644.
[11] Zhou W J,Wang K H,Wang J X. Atom-efficient palladium-catalyzed still coupling reaction of tetraphenylstannane with aryliodides or aryl bromides in polyethylene glycol 400(PEG-400)[J]. Adv Synth Catal,2009,351(9):1 378-1 382.
[12] Ueura K,Satoh T,Miura M. Rhodium-catalyzed arylation using arylboron compounds:efficient coupling with aryl halides and unexpected multiple arylation of benzonitrile[J]. Org Lett,2005,7(11):2 229-2 231.
[13] Bolliger J L,Frech C M. [Pd(Cl)2 {P(NC5 H10 ) (C6 H11 )2 }2 ]—A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings[ J]. Chem A Eur J,2010,16(36):11 072-11 081.
[14] Amatore M,Gosmini C. Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate[J]. Angew Chem Int Ed,2008,47(11):2 089-2 092.

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Last Update: 2014-06-30