An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism

V. D Vijaykumar Bodduri, Kyung Min Choi, Raghavender Rao Vaidya, Kalpesh Patil, Sridhar Chirumarry, Kiwan Jang, Yong Jin Yoon, J R Falck, Dong Soo Shin

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

A method involving iron catalyzed acylative cleavage of cyclic and acyclic ethers with acyl/aroyl chlorides has been studied to produce chloroesters and esters respectively. Examination of the scope revealed that less electron rich alkyl group in unsymmetric, acyclic ether was acylated while the chloride derived from the counterpart moiety was volatile and difficult to isolate. In contrast, α-branched cyclic ethers were converted to the corresponding primary ester and secondary chloride. Steric hindrance of ether also plays an important role in acylative C-O bond cleavage. The mechanism of ether cleavage is proposed to involve a single electron initiated SN1 dissociative pathway.

Original languageEnglish (US)
Pages (from-to)7089-7093
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number51
DOIs
StatePublished - Dec 23 2015

Keywords

  • Acylative ether cleavage
  • Chloroesters
  • Iron powder
  • S1 mechanism
  • Single electron transfer

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Bodduri, V. D. V., Choi, K. M., Vaidya, R. R., Patil, K., Chirumarry, S., Jang, K., Yoon, Y. J., Falck, J. R., & Shin, D. S. (2015). An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism. Tetrahedron Letters, 56(51), 7089-7093. https://doi.org/10.1016/j.tetlet.2015.11.016