Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 8, Pages 2039-2046Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201100142
Keywords
biaryldiazoacetates; catalysis; fluorenes; regioselectivity; rhodium
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Funding
- Korea Research Foundation [KRF-2008-C00024]
- MIRC [NRF-2010-0001957]
- NRF [R31-2008-000-10055-0]
- National Research Foundation of Korea [2009-0093123, R31-2011-000-10055-0] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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The rhodium- or copper-catalyzed intramolecular aromatic carbenoid insertion of biaryldiazoacetates offers a convenient route to fluorene carboxylates with high yields. Whereas, thermal conditions provided a mixture of two regioisomeric products when substituted biaryldiazoacetates were employed as substrates. The developed catalytic conditions displayed an excellent level of regioselectivity, presumably owing to steric effects. The insertion mechanism was assumed to be an electrophilic aromatic substitution, which was supported by preliminary mechanistic studies. A chloro-substituted fluorene derivative was efficiently synthesized and utilized as a base-sensitive protecting group of amines.
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