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Volumn 356, Issue 8, 2014, Pages 1767-1772

General methods for synthesis of N-methyliminodiacetic acid boronates from unstable ortho-phenolboronic acids

Author keywords

methoxymethyl (MOM) group; MIDA boronates; N methyliminodiacetic acid (MIDA); ortho phenolboronic acids; trimethylsilyl (TMS) chloride

Indexed keywords


EID: 84901295259     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201301023     Document Type: Article
Times cited : (10)

References (39)
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    • 84901319761 scopus 로고    scopus 로고
    • Based on a SciFinder substructure search using phenylboronic acid, more than 9000 phenylboronic acid derivatives are commercially available as of November 2013
    • Based on a SciFinder substructure search using phenylboronic acid, more than 9000 phenylboronic acid derivatives are commercially available as of November 2013.
  • 5
    • 84901375487 scopus 로고    scopus 로고
    • The numbers of commercially available ortho- and para-phenolboronic acid derivatives are 62 and 37, respectively, as of November 2013.
    • The numbers of commercially available ortho- and para-phenolboronic acid derivatives are 62 and 37, respectively, as of November 2013.
  • 9
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    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 2667-2672
  • 28
    • 80052305738 scopus 로고    scopus 로고
    • For the use of chiral MIDA boronates in diastereoselective synthesis, see:, J. Li, M. D. Burke, J. Am. Chem. Soc. 2011, 133, 13774-13777.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13774-13777
    • Li, J.1    Burke, M.D.2
  • 29
    • 84880557695 scopus 로고    scopus 로고
    • For the use of chiral MIDA boronates in diastereomeric resolution to access axially chiral compounds, see:, C.-Y. Lee, C.-H. Cheon, J. Org. Chem. 2013, 78, 7086-7092.
    • (2013) J. Org. Chem. , vol.78 , pp. 7086-7092
    • Lee, C.-Y.1    Cheon, C.-H.2
  • 30
    • 84901378028 scopus 로고    scopus 로고
    • More than 170 MIDA boronates are currently commercially available from Aldrich as of November 2013
    • More than 170 MIDA boronates are currently commercially available from Aldrich as of November 2013.
  • 31
    • 84901306337 scopus 로고    scopus 로고
    • When we started this research, meta-phenol MIDA boronate was already commercially available, while ortho- and para-phenol MIDA boronates were not commercialized at that time. However, para-phenol MIDA boronate 2f was commercialized by Aldrich very recently
    • When we started this research, meta-phenol MIDA boronate was already commercially available, while ortho- and para-phenol MIDA boronates were not commercialized at that time. However, para-phenol MIDA boronate 2f was commercialized by Aldrich very recently.
  • 32
    • 84901356257 scopus 로고    scopus 로고
    • MIDA 3 is not soluble in acetone, while the resulting phenol MIDA boronates 2 are soluble in acetone. Using the difference in solubility between 3 and 2, unreacted 3 could be easily recovered from the reaction mixture by simple filtration
    • MIDA 3 is not soluble in acetone, while the resulting phenol MIDA boronates 2 are soluble in acetone. Using the difference in solubility between 3 and 2, unreacted 3 could be easily recovered from the reaction mixture by simple filtration.
  • 33
    • 84901319195 scopus 로고    scopus 로고
    • The major by-product was the MIDA boronate from boric acid, which was one of the products of protodeboronation of 1.
    • The major by-product was the MIDA boronate from boric acid, which was one of the products of protodeboronation of 1.
  • 34
    • 84901333333 scopus 로고    scopus 로고
    • MIDA boronates 2 from boronic acids 1 and that from boric acid have similar solubility and polarity, which makes them very difficult to separate by conventional purification methods.
    • MIDA boronates 2 from boronic acids 1 and that from boric acid have similar solubility and polarity, which makes them very difficult to separate by conventional purification methods.
  • 37
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.