Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 16
492
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Tris(N,N-dimethylthiocarbamoyl)-1,1,1-tris-(methylaminomethyl)ethane and Its Application as Ligand for Pauson–Khand Reaction

, &
Pages 2761-2767 | Received 24 Oct 2007, Accepted 31 Oct 2007, Published online: 25 Aug 2010

REFERENCES

  • Yang , M ; Yip , K. T. ; Pan , J. H. ; Chen , Y. C. ; Zhu , N. Y. ; Yang , D. A sterically bulky cyclic thiourea as an efficient ligand for palladium-catalyzed aerobic oxidation of alcohols . Synlett 2006 , 3057 – 3060 .
  • Chen , W. ; Li , R. ; Wu , Y. ; Ding , L. S. ; Chen , Y. C. Self-supported thiourea–palladium complexes: Highly air-stable and recyclable catalysts for the Suzuki reaction in neat water. Synthesis 2006, 3058–3062; Chen, W.; Li, R.; Han, B.; Li, B. J.; Chen, Y. C.; Wu, Y. Ding, L. S.; Yang, D. The design and synthesis of bis(thiourea) ligands and their application in Pd-catalyzed Heck and Suzuki reactions under aerobic conditions. Eur. J. Org. Chem.. 2006, 1177–1184.
  • Yang , D. ; Chen , Y. C. ; Zhu, N. Y. Sterically bulky thioureas as air- and moisture-stable ligands for Pd-catalyzed Heck reactions of aryl halides . Org. Lett. 2004 , 6 , 1577 – 1580 .
  • Dai , M. J. ; Liang , B. ; Wang , C. H. ; You , Z. J. ; Xiang , J. ; Dong , G. B. ; Chen , J. H. ; Yang , Z. A novel thiourea ligand applied in the Pd-catalyzed Heck, Suzuki, and Suzuki carbonylative reactions . Adv. Synth. Catal. 2004 , 346 , 1669 – 1673 .
  • Dai , M. J. ; Wang , C. H. ; Dong , G. B. ; Xiang , J. ; Luo , T. P. ; Liang , B. ; Chen , J. H. ; Yang , Z. Development of thiourea-based ligands for the palladium-catalyzed bis(methoxycarbonylation) of terminal olefins . Eur. J. Org. Chem. 2003 , 4346 – 4348 .
  • Mukai , C. ; Yoshida , T. ; Sorimachi , M. ; Odani , A. CO2(CO)(8)-catalyzed intramolecular hetero–Pauson–Khand reaction of alkynecarbodiimide: Synthesis of (±)-physostigmine . Org. Lett. 2006 , 8 , 83 – 86 ; Tang, Y. F.; Zhang, Y. D.; Dai, M. J.; Luo, T. P.; Deng, L. J.; Chen, J. H.; Yang, Z. A highly efficient synthesis of the FGH ring of micrandilactone A: Application of thioureas as ligands in the co-catalyzed Pauson–Khand reaction and Pd-catalyzed carbonylative annulation. Org. Lett.. 2005, 7, 885–888; Tang, Y. F.; Deng, L. J.; Zhang, Y. D.; Dong, G. B.; Chen, J. H.; Yang, Z. Thioureas as ligands in the Pd-catalyzed intramolecular Pauson–Khand reaction. Org. Lett. 2005, 7, 1657–1659 .
  • Tang , Y. F. ; Deng , L. J. ; Zhang , Y. D. ; Dong , G. B. ; Chen , J. H. ; Yang , Z. Tetramethyl thiourea/Co-2(CO)(8)-catalyzed Pauson–Khand reaction under balloon pressure of CO . Org. Lett. 2005 , 7 , 593 – 595 .
  • Kinoshita , S. ; Kinoshita , H. ; Iwamura , T. ; Watanabe , S. ; Kataoka , T. Chalcogenide–Lewis acid mediated reactions of electron-deficient alkynes with aldehydes . Chem. Eur. J. 2003 , 9 , 1496 – 1502 .
  • Kasowski , W. J. ; Bailar , J. C. Steric effects in coordination of 1,1,1-tris(dimethylaminomethyl)ethane and of 1,1,1-tris(monomethylaminomethyl)ethane I: Zinc(2) complexes . J. Am. Chem. Soc. 1969 , 91 , 3212 – 3218 .
  • Herzog , H. L. Pentaerythrityl tetrabromide [propane, 1,3-dibromo-2,2-bis(Bromomethyl)-] . Org. Synth. 1951 , 31 , 82 – 84 .
  • Valente , A. A. ; Petrovski , Z. ; Branco , L. C. ; Afonso , C. A. M. ; Pillinger , M. ; Lopes , A. D. ; Romao , C. C. ; Nunes , C. D. ; Goncalves , I. S. Epoxidation of cyclooctene catalyzed by dioxomolybdenum(VI) complexes in ionic liquids . J. Mol. Catal. A—Chem. 2004 , 218 , 5 – 11 ; Petrovski, Z.; Valente, A. A.; Pillinger, M.; Dias, A. S.; Rodrigues, S. S.; Romao, C. C.; Goncalves, I. S. Molybdenum(VI) oxides bearing 1,4,7-triazacyclononane and 1,1,1-tris(aminomethyl)ethane ligands: Synthesis and catalytic applications. J. Mol. Catal. A—Chem. 2006, 249, 166–171. In our experience, the only case when 2 and its derivatives could not accompany triazacyclononane in reactivity was in reaction with Re2O7 .
  • Freyberger , A. ; Ahr , H. J. Studies on the goitrogenic mechanism of action of N,N,N',N'-tetramethylthiourea . Toxicology 2006 , 217 , 169 – 175 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.