Prev. Article Next Article Table of Contents

Note

Pd−C-Induced Catalytic Transfer Hydrogenation with Triethylsilane

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Pijus K. Mandal and John S. McMurray*

Department of Experimental Therapeutics, The University of Texas M. D. Anderson Cancer Center, 1515 Holcombe Blvd., Houston, Texas 77030 jsmcmur@mdanderson.org

J. Org. Chem., 2007, 72 (17), pp 6599–6601

DOI: 10.1021/jo0706123

Publication Date (Web): July 14, 2007

Section:

General Organic Chemistry

Abstract

In situ generation of molecular hydrogen by addition of triethylsilane to palladium−charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 35 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 9 ACS Journal articles (5 most recent appear below).

Chiral Pyridin-3-ones and Pyridines: Syntheses of Enantiopure 2,4-Disubstituted 6-Hydroxy-1,6-Dihydro-2H-Pyridin-3-ones, 2,3-Disubstituted 4-Iodopyridines, and Enantiopure 2,3-Disubstituted 4-Pyridinemethanols
Irfan Husain, Mohammad Saquib, Vikas Bajpai, Brijesh Kumar, and Arun K. Shaw
The Journal of Organic Chemistry2011 76 (21), 8930-8943
- Chiral Pyridin-3-ones and Pyridines: Syntheses of Enantiopure 2,4-Disubstituted 6-Hydroxy-1,6-Dihydro-2H-Pyridin-3-ones, 2,3-Disubstituted 4-Iodopyridines, and Enantiopure 2,3-Disubstituted 4-Pyridinemethanols
  Irfan Husain, Mohammad Saquib, Vikas Bajpai, Brijesh Kumar, and Arun K. Shaw
  The Journal of Organic Chemistry2011 76 (21), 8930-8943
  The development of an innovative method to access enantiopure 2,4-disubstituted 6-hydroxy-1,6-dihydro-2H-pyridin-3-ones starting from d-glucal via the aza-Achmatowicz transformation has been described. These highly functionalized pyridin-3-ones have been ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides
Nisha V. Handa, Kayla D. Mendoza, and Laura D. Shirtcliff
Organic Letters2011 Article ASAP
- Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides
  Nisha V. Handa, Kayla D. Mendoza, and Laura D. Shirtcliff
  Organic Letters2011 Article ASAP
  Via Sonogashira cross-coupling with different alkynes, 1,6 and 1,7 perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) were synthesized from the corresponding regioisomeric mixture of 1,6/1,7-dibromo precursors. Both bulky triphenyl ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Selective Synthesis of 7-Substituted Purines via 7,8-Dihydropurines
Vladislav Kotek, Naděžda Chudíková, Tomáš Tobrman, and Dalimil Dvořák
Organic Letters2010 12 (24), 5724-5727
- Selective Synthesis of 7-Substituted Purines via 7,8-Dihydropurines
  Vladislav Kotek, Naděžda Chudíková, Tomáš Tobrman, and Dalimil Dvořák
  Organic Letters2010 12 (24), 5724-5727
  A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N7-alkylation followed by N9-trityl deprotection ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Synthesis of Aminooxy and N-Alkylaminooxy Amines for Use in Bioconjugation
Michael R. Carrasco, Carolina I. Alvarado, Scott T. Dashner, Amanda J. Wong and Michael A. Wong
The Journal of Organic Chemistry2010 75 (16), 5757-5759
- Synthesis of Aminooxy and N-Alkylaminooxy Amines for Use in Bioconjugation
  Michael R. Carrasco, Carolina I. Alvarado, Scott T. Dashner, Amanda J. Wong and Michael A. Wong
  The Journal of Organic Chemistry2010 75 (16), 5757-5759
  Five Boc-protected aminooxy and N-alkylaminooxy amines have been synthesized in 60−95% overall yield using a common synthetic strategy from readily available two- and three-carbon Cbz-protected amino alcohols. The amines can be linked to biomolecules via ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Synthesis of C-Propargylic Esters of N-Protected Amino Acids and Peptides
Sean P. Bew and Glyn D. Hiatt-Gipson
The Journal of Organic Chemistry2010 75 (11), 3897-3899
- Synthesis of C-Propargylic Esters of N-Protected Amino Acids and Peptides
  Sean P. Bew and Glyn D. Hiatt-Gipson
  The Journal of Organic Chemistry2010 75 (11), 3897-3899
  Recent years have seen a huge surge of interest in the application of alkyne-derived motifs for so-called “click” chemistry. Given the critical importance of amino acids in organic synthesis as well as their myriad of applications in “click” chemistry it ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links