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- Title
Scope and Limitations of the Intermolecular Furan-Yne Cyclization.
- Authors
Zeiler, Anna; Ziegler, Michael J.; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.
- Abstract
Different types of alkynes were reacted with 2,5-disubstituted furans in order to evaluate the scope of the intermolecular furan-yne reaction. With ethynyl aryl ethers as starting materials, 2-phenoxy phenols were accessible in moderate to good yields. A different reaction mode was observed for alkynes bearing electron-withdrawing substituents. For these starting materials a cis-selective hydroarylation took place in an anti-Markovnikov fashion in excellent yields. 1,2-Diynes turned out to be suitable starting materials as well. Due to the second alkynyl moiety, after an initial phenol synthesis, a subsequent hydro-alkoxylation by the newly formed phenolic oxygen gives access to benzofurans in a tandem process.
- Subjects
RING formation (Chemistry); FURAN derivatives; ALKYNES; PHENOL synthesis; ARYLATION
- Publication
Advanced Synthesis & Catalysis, 2015, Vol 357, Issue 7, p1507
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201500081