期刊
TETRAHEDRON
卷 67, 期 41, 页码 8014-8026出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.08.019
关键词
Annulation; Aromatic hydrocarbons; Boron; Cross-coupling reaction; Palladium
资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan [16GS0209]
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [10J05440] Funding Source: KAKEN
This study demonstrates that the double cross-coupling reaction of 1,2-bis(pinacolatoboryl)alkenes and -arenes with 2,2'-dibromobiaryls proceeds smoothly with the aid of a catalytic amount of Pd(PPh3)(4) in the presence of excess base to give a variety of polycyclic aromatic hydrocarbons, such as phenanthrenes, [5]helicene, dithienobenzenes, triphenylenes, dibenzo[g,p]chrysenes, and triphenyleno[1,2-b:4,3-b']di-thiophenes in good to high yields. It is noteworthy that the annulations using 2,2'-dibromoocta-fluorobiphenyl as an electrophile furnish the otherwise difficult to synthesize octafluorophenanthrenes and semi-fluorinated dibenzo[g,p]chrysenes in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
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