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Volumn 13, Issue 30, 2015, Pages 8298-8309

Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; PEPTIDES;

EID: 84937694131     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c5ob01174d     Document Type: Article
Times cited : (58)

References (48)
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    • An elegant example of the Suzuki-Miyuara reaction performed on proteins containing genetically incorporated aryl iodides can be found in.
    • K. C. Nicolaou P. G. Bulger D. Sarlah Angew. Chem., Int. Ed. 2005 44 4442
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 4442
    • Nicolaou, K.C.1    Bulger, P.G.2    Sarlah, D.3
  • 23
    • 84941054992 scopus 로고    scopus 로고
    • We have established that when the Ackermann conditions ([Ph2I]OTs, DMF, 100°C, 17 h) are applied to the protected tryptophan 1a, no C2-arylation is observed. Addition of Pd(OAc)2 (5 mol%) afforded 93% conversion to the desired arylation product 2a. Air has no appreciable effect
    • Y. Zhu M. Bauer J. Ploog L. Ackermann Chem.-Eur. J. 2014 20 13099
    • (2014) Chem.-Eur. J. , vol.20 , pp. 13099
    • Zhu, Y.1    Bauer, M.2    Ploog, J.3    Ackermann, L.4
  • 24
    • 33646137411 scopus 로고    scopus 로고
    • We have also established that the reaction of 1a with either 4-Me-C6H4B(OH)2 or 4-OMe-C6H4B(OH)2 and PhI(OAc)2 affords a similar mixture of 2-arylated tryptophan products in a ca. 1:1 ratio by ESI-HRMS For selected papers on hydroxylation of organic compounds by C-H bond activation with CuII/O2 systems, see
    • N. R. Deprez D. Kalyani A. Krause M. S. Sanford J. Am. Chem. Soc. 2006 128 4972
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4972
    • Deprez, N.R.1    Kalyani, D.2    Krause, A.3    Sanford, M.S.4
  • 29
    • 2842520240 scopus 로고
    • The X-ray single crystal structure of l-(trypthophyl-glycinato)copper(ii) shows how a free carboxylate amino acid neighbouring a tryptophan can coordinate CuII, see
    • H. Borsook K. V. Thimann J. Biol. Chem. 1932 98 671
    • (1932) J. Biol. Chem. , vol.98 , pp. 671
    • Borsook, H.1    Thimann, K.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.