Multifunctional Crown-5-calix[4]arene-based Phase-Transfer Catalysts for Aromatic 18F-Fluorination

  • Lee, Won Chang; 
  • Kang, Seok Min; 
  • Lee, Byung Chul; 
  • Kim, Sang Eun; 
  • Kim, Dong Wook
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초록

Methylated bis-triethylene glycolic crown-5-calix[4]arene (M-BTC5A) as a phase-transfer catalyst showed the best performance among other analogues and even conventional Kryptofix 222 in the nucleophilic aromatic F-18-fluorination of diaryliodonium tosylate precursors owing to (i) the efficient release of reactive "naked" [F-18]fluoride, (ii) the high stabilization of the precursor in the reaction, and, presumably, (iii) the ease of access between the precursor and the (KF)-F-18/M-BTC5A complex facilitated by p-p interactions. [F-18]Flumazenil was produced in high radiochemical yield using M-BTC5A.

키워드

POSITRON-EMISSION-TOMOGRAPHY; OLIGOETHYLENE GLYCOLS; LATE-STAGE; FLUORINE; RADIOFLUORINATION; SUBSTITUTION; SALTS; PHARMACEUTICALS; STRATEGIES; PROMOTERS
제목
Multifunctional Crown-5-calix[4]arene-based Phase-Transfer Catalysts for Aromatic 18F-Fluorination
저자
Lee, Won Chang; Kang, Seok Min; Lee, Byung Chul; Kim, Sang Eun; Kim, Dong Wook
DOI
10.1021/acs.orglett.0c03604
발행일
2020-12-18
유형
Article
저널명
Organic Letters
권
22
호
24
페이지
9551 ~ 9555