Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides

Jinkui Chai, Wei Ding, Chen Wang, Shingo Ito, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The Ritter reaction, Brønsted- or Lewis acid-mediated amidation of alkene or alcohol with nitrile via a carbocation, represents a classical method for the synthesis of tertiary amides. Although analogous reactions through a vinyl cation or a species alike may offer a route to enamide, an important synthetic building block as well as a common functionality in bioactive compounds, such transformations remain largely elusive. Herein, we report a Ritter-type trans-difunctionalization of alkynes with a trivalent iodine electrophile and nitrile, which affords β-iodanyl enamides in moderate to good yields. Mediated by benziodoxole triflate (BXT), the reaction proves applicable to a variety of internal alkynes as well as to various alkyl- and arylnitriles. The benziodoxole group in the product serves as a versatile handle for further transformations, thus allowing for the preparation of various tri- and tetrasubstituted enamides that are not readily accessible by other means. This journal is

Original languageEnglish
Pages (from-to)15128-15133
Number of pages6
JournalChemical Science
Volume12
Issue number45
DOIs
Publication statusPublished - 2021 Dec 7

ASJC Scopus subject areas

  • Chemistry(all)

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