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Volumn 64, Issue 11, 2008, Pages 2537-2552

Pd(OAc)2-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes

Author keywords

1,2 Dihalobenzenes; 2 Haloaryl arenesulfonates; Domino reactions; Grignard reagents; Palladium; Substituted fluorenes

Indexed keywords

1 BROMO 2 BROMOBENZENE; 1 BROMO 2 CHLOROBENZENE; 1 BROMO 2 FLUOROBENZENE; 1 BROMO 2 IODOBENZENE; 1,2 DIBROMOBENZENE; 1,2 DIHALOARENE DERIVATIVE; 2 BROMO 4 METHYLPHENYLTOSYLATE; 2 CHLORO 4 METHYLPHENYLTOSYLATE; 2 HALOARYL ARENESULFONATE DERIVATIVE; 2 IODO 4 METHYLPHENYLTOSYLATE; 2,4 DIMETHYLFLUORENE; ALKYNE DERIVATIVE; BENZENE DERIVATIVE; CARBENE; FLUORENE DERIVATIVE; GRIGNARD REAGENT; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 38749132948     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.020     Document Type: Article
Times cited : (30)

References (110)
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    • Fluorene is the core structure of biologically active molecules, sensors and light-emitting materials. For examples, see:
    • Fluorene is the core structure of biologically active molecules, sensors and light-emitting materials. For examples, see:
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    • 3 C-H activation are rare: Ref. 4. Also see:
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    • For examples on Pd-catalyzed tandem/domino cross-coupling-cyclization via aromatic C-H bond activation, see:
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    • For recent general reviews on tandem/domino reactions, see:
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    • Recent examples of annulative tandem reactions based on transition metal-catalyzed addition/cross-coupling strategies:
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    • Recent examples of Pd-catalyzed reactions via carbopalladation of arynes:
    • Recent examples of Pd-catalyzed reactions via carbopalladation of arynes:
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    • Recent examples of Pd-catalyzed cyclotrimerization of arynes:
    • Recent examples of Pd-catalyzed cyclotrimerization of arynes:
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    • For recent examples of Pd-catalyzed carbonylation of arynes, see:
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    • n have been reported:
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    • For examples of Pd(IV) palladacycles as intermediates, see:
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    • note
    • 2-catalyzed reaction of 1,2-dichlorobenzene with 2-mesitylmagnesium bromide in THF at 60 °C gave low yield of 2,4-dimethylfluorene (24%, much lower than the 95% yield observed for 1-bromo-2-chlorobenzene under the same reaction condition), indicating that the initial oxidative addition at the C-Cl bond occurred very slowly. This observation suggested that with 1-bromo-2-chlorobenzene as substrate, the initial oxidative addition should mainly take place at the C-Br bond.
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    • Recent reviews for N-heterocyclic carbenes as Pd(0) ligands:
    • Recent reviews for N-heterocyclic carbenes as Pd(0) ligands:
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    • Aryl C-F bond is known to be inert for oxidative addition. For examples of Pd-catalyzed cross-coupling reaction of activated aryl fluorides, see:
    • Aryl C-F bond is known to be inert for oxidative addition. For examples of Pd-catalyzed cross-coupling reaction of activated aryl fluorides, see:
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    • Two isomeric products in close to 1:1 ratio were always observed with unsymmetrical arynes in the reported aryne generation strategy from o-trimethylsilylaryl triflates, see Ref. 13.
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    • Whether the formation of arynes would be assisted by the Grignard reagents remains unclear to us at present. Bases were found to be influential on the β-elimination of (2-halo)alkenylPd(II)X complexes:
    • Whether the formation of arynes would be assisted by the Grignard reagents remains unclear to us at present. Bases were found to be influential on the β-elimination of (2-halo)alkenylPd(II)X complexes:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.