메뉴 건너뛰기




Volumn 11, Issue 15, 2009, Pages 3174-3177

Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

Author keywords

[No Author keywords available]

Indexed keywords

BENZOYL PEROXIDE; CARBON; HYDROGEN; ORGANOMETALLIC COMPOUND; PALLADIUM;

EID: 68149126733     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900756g     Document Type: Article
Times cited : (179)

References (52)
  • 46
    • 68149097972 scopus 로고    scopus 로고
    • Experimental Procedure. Method A: A mixture of substrate (0.5 mmol, Pd(OAc)2 (0.025 mmol, 5 mol , and benzoyl peroxide (1 mmol; addition interval 4 × 0.5 equiv/0.5 h) in acetonitrile (1 mL) and acetic acid (1 mL) was sealed in a 8 mL vial with a Teflon-lined cap. The mixture was heated at 100 °C (oil bath temperature) for 2 h. Method B: A mixture of substrate (0.5 mmol, Pd(OAc)2 (0.025 mmol, 5 mol , and benzoyl peroxide (1 mmol) in acetonitrile (1 mL) and acetic acid (1 mL) was sealed in a 8 mL vial with a Teflon-lined cap. The mixture was heated at 160 °C (oil bath temperature) for 10 min. Method C: A mixture of substrate (0.5 mmol, Pd(OAc)2 (0.05 mmol, 10 mol , and benzoyl peroxide (1 mmol) in acetonitrile (2 mL) was sealed in a 8 mL vial with a Teflon-lined cap. The mixture was heated at 160 °C (oil bath temperature) for 10 min. Caution: Aryl acylperoxides are potentially explosive and should be handled with c
    • 2 (0.05 mmol, 10 mol %), and benzoyl peroxide (1 mmol) in acetonitrile (2 mL) was sealed in a 8 mL vial with a Teflon-lined cap. The mixture was heated at 160 °C (oil bath temperature) for 10 min. Caution: Aryl acylperoxides are potentially explosive and should be handled with care and in small quantities.
  • 47
    • 68149118459 scopus 로고    scopus 로고
    • 2 catalyst, la (87%) was recovered with trace quantities of isomeric o-, m-, and p-arylated products being observed by GC-MS.
    • 2 catalyst, la (87%) was recovered with trace quantities of isomeric o-, m-, and p-arylated products being observed by GC-MS.
  • 48
    • 68149086921 scopus 로고    scopus 로고
    • Performing the arylation of oximes in MeCN/AcOH medium produced a complicated mixture, and extensive hydrolysis of the oximes was observed (see Table S10 in Supporting Information for results).
    • Performing the arylation of oximes in MeCN/AcOH medium produced a complicated mixture, and extensive hydrolysis of the oximes was observed (see Table S10 in Supporting Information for results).
  • 49
    • 68149115341 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 50
    • 68149105308 scopus 로고    scopus 로고
    • With 2-methoxylbenzoyl peroxide as reagent, no arylation but carboxylation products formation was observed with recovery of la
    • With 2-methoxylbenzoyl peroxide as reagent, no arylation but carboxylation products formation was observed with recovery of la.
  • 51
    • 0000139820 scopus 로고    scopus 로고
    • A plausible alternative route to arylcarboxylation is via oxidative addition of the peroxide to Pd(II) to give a reactive Pd(IV) species, which would subsequently undergo reductive elimination; see: Canty, A. J.; Jin, H.; Skelton, B. W.; White, A. H. Inorg. Chem. 1998, 37, 3975.
    • A plausible alternative route to arylcarboxylation is via oxidative addition of the peroxide to Pd(II) to give a reactive Pd(IV) species, which would subsequently undergo reductive elimination; see: Canty, A. J.; Jin, H.; Skelton, B. W.; White, A. H. Inorg. Chem. 1998, 37, 3975.
  • 52
    • 67949109328 scopus 로고    scopus 로고
    • Ritter and co-workers disclosed a radical mechanism for the Pd(OAc)2-catalyzed heteroatom C-H functionalization, and formation of a Pd(III) -Pd(III) intermediate was proposed; see: Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302-309.
    • Ritter and co-workers disclosed a radical mechanism for the Pd(OAc)2-catalyzed heteroatom C-H functionalization, and formation of a Pd(III) -Pd(III) intermediate was proposed; see: Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302-309.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.