Direct oxidative heck cyclizations: Intramolecular Fujiwara-Moritani arylations for the synthesis of functionalized benzofurans and dihydrobenzofurans

Angewandte Chemie - International Edition

Volumn 43, Issue 45, 2004, Pages 6144-6148

  Zhang, Haiming ^a   Ferreira, Eric M ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

Benzofurans; Homogeneous catalysis; Oxidation; Palladium

Indexed keywords

CATALYSIS; DEHYDROGENATION; DERIVATIVES; PALLADIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMOOXIDATION;

BENZOFURAN; CARBOCYCLIZATIONS; DIHYDROBENZOFURAN; HECK CYCLIZATIONS;

FURAN RESINS;

ACID; ALKENE; BENZENE; BENZOFURAN DERIVATIVE; BENZOQUINONE; DIHYDROBENZOFURAN DERIVATIVE; HALIDE; INDOLE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; VINYL DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DEHYDROGENATION; DIASTEREOISOMER; FUJIWARA MORITANI REACTION; HALOGENATION; HECK REACTION; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

BENZOFURANS; CYCLIZATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 10044267678     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461294     Document Type: Article

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52. A screen of solvents and ligands was also conducted, but provided no improvements. These parameters were investigated extensively in our indole system.[8]
53. Pd-promoted aryl Claisen rearrangements appear not to be generally competitive, and no such products were isolated in any of the reactions in Tables 3 and 4. Only one such case, involving the reaction of a 1-allyloxynaphthalene derivative, has been observed under our conditions.
54. In addition to 5, a small amount of starting ether 3 was isolated. No other isomeric products were observed in the reaction.
55. A similar observation was made in our studies directed toward the oxidative annulation of indoles.[8]
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