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Volumn 60, Issue 7, 2017, Pages 343-348

Burgess iridium(I)-catalyst for selective hydrogen isotope exchange

Author keywords

Burgess catalyst; CH activation; deuterium; hydrogen isotope exchange

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID; DEUTERIUM; FLUOROBENZENE; HYDROGEN; IMIDAZOLE; IRIDIUM; KETONE; OXAZOLE; PYRAZINE; PYRIDINE;

EID: 85019179597     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.3512     Document Type: Article
Times cited : (33)

References (56)
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    • For recent selected examples, see a
    • For recent selected examples, see: a)Hatano M, Nishimura T, Yorimitsu H. Org Lett. 2016;18(15):3674-3677;
    • (2016) Org Lett , vol.18 , Issue.15 , pp. 3674-3677
    • Hatano, M.1    Nishimura, T.2    Yorimitsu, H.3
  • 26
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    • For selected reviews, see a
    • For selected reviews, see: a)Salter R. J Label Compd Radiopharm. 2010;53:645-657;
    • (2010) J Label Compd Radiopharm , vol.53 , pp. 645-657
    • Salter, R.1
  • 51
    • 85020590456 scopus 로고    scopus 로고
    • We propose that 2-MeTHF coordinates to the iridium catalyst in competition to the substrate. In comparison to MTBE the coordination seems to be much stronger as demonstrated by deuterium introduction of <20% with model compounds 7,8 and
    • We propose that 2-MeTHF coordinates to the iridium catalyst in competition to the substrate. In comparison to MTBE the coordination seems to be much stronger as demonstrated by deuterium introduction of <20% with model compounds 7,8 and 9.
  • 52
    • 85020590542 scopus 로고    scopus 로고
    • The transition state seems to work only in a five membered ring iridium-arene complex (for the peri position) and not via a four-membered ring necessary to exchange the hydrogen in the 2, position of 1-naphthylamine 9
    • The transition state seems to work only in a five membered ring iridium-arene complex (for the peri position) and not via a four-membered ring necessary to exchange the hydrogen in the 2-position of 1-naphthylamine 9.
  • 53
    • 85020580624 scopus 로고    scopus 로고
    • A faster and more efficient deuterium exchange was observed in the kinetic study as compared to the screening results in table 2 under similar conditions (entry 3 after 2 h). The reason for this small discrepancy may be a different experimental set-up with Heidolph parallel Synthesizer (with shacking) utilized for all screening reactions in contrast to the kinetic studies performed in a 50 mL flask with stirring
    • A faster and more efficient deuterium exchange was observed in the kinetic study as compared to the screening results in table 2 under similar conditions (entry 3 after 2 h). The reason for this small discrepancy may be a different experimental set-up with Heidolph parallel Synthesizer (with shacking) utilized for all screening reactions in contrast to the kinetic studies performed in a 50 mL flask with stirring.
  • 54
    • 85020580673 scopus 로고    scopus 로고
    • We did not observe deuterium pressure dependency in any of our performed iridium-catalyzed HIE reactions
    • We did not observe deuterium pressure dependency in any of our performed iridium-catalyzed HIE reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.