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Volumn 27, Issue 13, 2008, Pages 3043-3055

Base-promoted selective activation of benzylic carbon-hydrogen bonds of toluenes by iridium(III) porphyrin

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; IRIDIUM; IRIDIUM COMPOUNDS; NONMETALS; PORPHYRINS; TOLUENE;

EID: 47949133017     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700751h     Document Type: Article
Times cited : (36)

References (74)
  • 38
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    • Lide, D. R, Ed, 85th ed; CRC Press: Cleveland, OH
    • Lide, D. R., Ed. CRC Handbook of Chemistry and Physics, 85th ed; CRC Press: Cleveland, OH, 2004.
    • (2004) CRC Handbook of Chemistry and Physics
  • 42
    • 47949114862 scopus 로고    scopus 로고
    • In the internal electrophilic substitution (IES) mechanism, the lone pair on an M-X ligand forms an X-H bond, while the orbital making up the M-X bond turns into a coordinating lone pair ref 12
    • In the internal electrophilic substitution (IES) mechanism, the lone pair on an M-X ligand forms an X-H bond, while the orbital making up the M-X bond turns into a coordinating lone pair (ref 12).
  • 49
    • 0000793905 scopus 로고    scopus 로고
    • Transition-metal coordinated CO can be reduced by hydride sources to yield metal-methyl complexes, (a) Treichel, P. M.; Shubkin, R. L. Inorg. Chem. 1967, 6, 1328-1334.
    • Transition-metal coordinated CO can be reduced by hydride sources to yield metal-methyl complexes, (a) Treichel, P. M.; Shubkin, R. L. Inorg. Chem. 1967, 6, 1328-1334.
  • 51
    • 47949120441 scopus 로고    scopus 로고
    • The carbonyl group of Rh(ttp)C(O)Ph was proposed to be reduced by Rh(ttp)H to yield Rh(Kp)Bn (ref 8).
    • The carbonyl group of Rh(ttp)C(O)Ph was proposed to be reduced by Rh(ttp)H to yield Rh(Kp)Bn (ref 8).
  • 52
    • 0038140455 scopus 로고    scopus 로고
    • The authentic sample of [Ir(ttp)]2 was synthesized using the same method to synthesize [Ir(oep)]2 by reacting Ir(oep)2 and TEMPO, a) Chan, K. S, Leung, Y.-B. Inorg. Chem. 1994, 3, 3187. The chemical shifts and splitting patterns of [Ir(ttp, 2 in 1H NMR spectrocscopy was similar to that of [Rh(ttp)]2. For [Ir(ttp)]2: 1H NMR (C 6D6) δ 9.48 (d, 4 H, o-phenyl, 8.33 (s, 8 H, pyrrole, 7.65 (d, 4 H, o′-phenyl, 2.46 (s, 12 H, p-methyl, m and m′-phenyl hydrogens are obscured by solvent (7.15, For [Rh(ttp)]2: 1H NMR (C 6D6) δ 9.64 (d, 4 H, o-phenyl, 8.63 (s, 8 H, pyrrole, 7.75 (d, 4 H, o′-phenyl, 2.50 (s, 12 H, p-methyl, m and m′-phenyl hydrogens are obscured by solvent 7.15
    • 6) δ 9.64 (d, 4 H, o-phenyl), 8.63 (s, 8 H, pyrrole), 7.75 (d, 4 H, o′-phenyl), 2.50 (s, 12 H, p-methyl); m and m′-phenyl hydrogens are obscured by solvent (7.15).
  • 54
    • 0010101224 scopus 로고    scopus 로고
    • An analogue of Ir(ttp)C(O)Ir(ttp, Rh(oep)C(O)Rh(oep, had been reported, a) Wayland, B. B, Woods, B. A, Coffin, V. L. Organometallics, 1986, 5, 1059-1062
    • An analogue of Ir(ttp)C(O)Ir(ttp), Rh(oep)C(O)Rh(oep), had been reported. (a) Wayland, B. B.; Woods, B. A.; Coffin, V. L. Organometallics, 1986, 5, 1059-1062.
  • 59
    • 47949130571 scopus 로고    scopus 로고
    • The reduction of a carbonyl ligand coordinated to transition metal to yield methyl ligand had been reported to proceed via a metal-formyl intermediate. Thus, Ir(ttp)CHO was proposed to be formed in the reduction of Ir(ttp)Cl(CO) by Ir(ttp)H.25b
    • 25b
  • 68
    • 34250809604 scopus 로고    scopus 로고
    • The difference between σ-complex-assisted metathesis and classical σ-bond metathesis in CHA is that the former involves the pre-coordination of the C-H bond to the metal center before concerted bond rearrangement, whereas the latter involves the direct concerted rearrangement of bonds. Perutz, R. N, Sabo-Etienne, S. Angew. Chem, Int. Ed. 2007, 46, 2578-2592
    • The difference between σ-complex-assisted metathesis and classical σ-bond metathesis in CHA is that the former involves the pre-coordination of the C-H bond to the metal center before concerted bond rearrangement, whereas the latter involves the direct concerted rearrangement of bonds. Perutz, R. N.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2007, 46, 2578-2592.
  • 71
    • 47949095273 scopus 로고    scopus 로고
    • An anologue of Ir(ttp)H, Rh(oep)H, was in equilibrium with [Rh(oep, 2 and H2 ref 32
    • 2 (ref 32).
  • 72
    • 47949120666 scopus 로고    scopus 로고
    • Isaacs, N. S. Physical Organic Chemistry; ELBS, Longman: Avon, U.K., 1987.
    • Isaacs, N. S. Physical Organic Chemistry; ELBS, Longman: Avon, U.K., 1987.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.