Journal
TETRAHEDRON
Volume 67, Issue 4, Pages 689-697Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.11.081
Keywords
Suzuki-Miyaura cross-coupling; Selectivity; Arylnaphthalenes; Substituent effect; Nucleophilicity; Aromatic interactions
Categories
Funding
- European Community [POCI/QUI/61873/2004]
- FCT
- European Social Fund (ESF)
- Community Support Framework (CSF) [SRFH/BD/29394/2006]
- Fundação para a Ciência e a Tecnologia [POCI/QUI/61873/2004] Funding Source: FCT
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A series of 1-arylnaphthalenes and 1,8-diarylnaphthalenes were synthesized by the Suzuki-Miyaura cross-coupling methodology showing significant differentiation in the yields and selectivity between aryl rings with electron donating (higher yields), and electron withdrawing substituents (lower yields). These results strongly support the relation between the nucleophilicity of the boronate complex and its reactivity, and emphasize the importance of the transmetalation step in the overall efficiency of this cross-coupling reaction. The results obtained with non-symmetric 1,8-diarylnaphthalenes indicate preference for arylation of an already arylated species (the 1-aryl-8-bromonaphthalene intermediate) over mono-arylation of 1,8-dibromonaphthalene. Evidences for the existence of intramolecular Pd center dot center dot center dot pi and aromatic interactions in some Pd(II) complexes were found. (C) 2010 Elsevier Ltd. All rights reserved.
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