Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2007 Apr 13;72(8):3125-8.
doi: 10.1021/jo0622173. Epub 2007 Mar 17.

Improved method for the diimide reduction of multiple bonds on solid-supported substrates

Keith R Buszek  1 , Neil Brown
Affiliations

Improved method for the diimide reduction of multiple bonds on solid-supported substrates

Keith R Buszek et al. J Org Chem. .

Abstract

A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron-poor olefins, and terminal alkynes were the most easily reduced.

PubMed Disclaimer

Figures

SCHEME 1
SCHEME 1
SCHEME 2
SCHEME 2
SCHEME 3
SCHEME 3
See this image and copyright information in PMC

References

    1. Dolle RE. J. Comb. Chem. 2005;7:739. - PubMed

    1. For an example of a multipolymer solution-phase reaction: Harned AM, He HS, Toy PH, Flynn DL, Hanson PR. J. Am. Chem. Soc. 2005;127:52..

    1. An example of a Lindlar reduction on a non-cross-linked polystyrene support has been reported: Chen S, Janda KD. J. Am. Chem. Soc. 1997;119:8724.Chen S, Janda KD. Tetrahedron Lett. 1998;39:3943. For catalytic homogeneous hydrogenation with Wilkinson's catalyst on a Rink resin, see: Whelan AN, Elaridi J, Harte M, Smith SV, Jackson WR, Robinson AJ. Tetrahedron Lett. 2004;45:9545..

    1. For a review of methods for generating diimide and its use in the reduction of multiple bonds in homogeneous environments, see: Pasto DJ, Taylor RT. Org. React. 1991;40:91.Miller CE. J. Chem. Ed. 1965;42:254..

    1. Buszek KR, Sato N, Jeong Y. J. Am. Chem. Soc. 1994;116:5511.
    2. Buszek KR, Jeong Y. Tetrahedron Lett. 1995;36:5677.
    3. Perchellet J-P, Perchellet EM, Newell SW, Freeman JA, Ladesich JB, Jeong Y, Sato N, Buszek KR. Anticancer Res. 1998;18:97. - PubMed
    4. Buszek KR, Sato N, Jeong Y, Sill PC, Muino PL, Ghosh I. Synth. Commun. 2001;31:1781.
    5. Buszek KR, Sato N, Jeong Y. Tetrahedron Lett. 2002;43:181.

Publication types