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Volumn 351, Issue 1-2, 2009, Pages 71-77

The first thiadiazolidine 1-oxide system for phosphine-free palladium-mediated catalysis

Author keywords

C C coupling; Catalysis; Mizoroki Heck reaction; Palladium; Thiadiazolidines

Indexed keywords


EID: 58549094517     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800522     Document Type: Article
Times cited : (15)

References (90)
  • 8
    • 34547130040 scopus 로고    scopus 로고
    • and references cited therein
    • S. E. Denmark, J. R. Heemstra, J. Org. Chem. 2007, 72, 5668, and references cited therein.
    • (2007) J. Org. Chem , vol.72 , pp. 5668
    • Denmark, S.E.1    Heemstra, J.R.2
  • 21
    • 0042034174 scopus 로고    scopus 로고
    • Z.; Regainia, M. Abdaoui, N. E. Aouf, G. Dewynter, J. L. Montero, Tetrahedron 2000, 56, 381.
    • c) Z.; Regainia, M. Abdaoui, N. E. Aouf, G. Dewynter, J. L. Montero, Tetrahedron 2000, 56, 381.
  • 33
    • 58549106700 scopus 로고    scopus 로고
    • For useful reviews covering different aspects of Heck chemistry see for example: a R. F. Heck, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, 4;
    • For useful reviews covering different aspects of Heck chemistry see for example: a) R. F. Heck, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, Vol. 4;
  • 40
    • 0003969056 scopus 로고    scopus 로고
    • Ed, L. S. Liebeskind, JAI Press Inc, Greenwich, CT
    • g) T. Jeffery, in: Advances in Metal-Organic Chemistry, (Ed.: L. S. Liebeskind), JAI Press Inc, Greenwich, CT, 1996, Vol. 5;
    • (1996) Advances in Metal-Organic Chemistry , vol.5
    • Jeffery, T.1
  • 48
    • 0003748618 scopus 로고    scopus 로고
    • Eds, S. G. Davies, S.-I. Murahashi, Blackwell Science, Oxford
    • o) M. T. Reetz, in: Transition Metal Catalyzed Reactions, (Eds.: S. G. Davies, S.-I. Murahashi), Blackwell Science, Oxford, 1999;
    • (1999) Transition Metal Catalyzed Reactions
    • Reetz, M.T.1
  • 61
    • 0034928699 scopus 로고    scopus 로고
    • For recent reviews on palladacycles for Heck reactions, see: a
    • For recent reviews on palladacycles for Heck reactions, see: a) J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917;
    • (2001) Eur. J. Inorg. Chem , pp. 1917
    • Dupont, J.1    Pfeffer, M.2    Spencer, J.3
  • 63
    • 0000906649 scopus 로고    scopus 로고
    • For the use of tetraphenylphosphonium salts in Heck reactions, see
    • For the use of tetraphenylphosphonium salts in Heck reactions, see: M. T. Reetz, G. Lohmer, R. Schwickardi, Angew. Chem. 1998, 110, 492;
    • (1998) Angew. Chem , vol.110 , pp. 492
    • Reetz, M.T.1    Lohmer, G.2    Schwickardi, R.3
  • 65
    • 58549099391 scopus 로고    scopus 로고
    • For recent reviews on N-heterocyclic carbene-palladium catalysts, see: a W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
    • For recent reviews on N-heterocyclic carbene-palladium catalysts, see: a) W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
  • 68
    • 0033537057 scopus 로고    scopus 로고
    • for recent reports on Heck reactions using catalysts that are air- and moisture-stable, see: c M. R. Buchmeiser, K. Wurst, J. Am. Chem. Soc. 1999, 121, 11101;
    • for recent reports on Heck reactions using catalysts that are air- and moisture-stable, see: c) M. R. Buchmeiser, K. Wurst, J. Am. Chem. Soc. 1999, 121, 11101;
  • 83
    • 58549104255 scopus 로고    scopus 로고
    • Using a Biotage Initiator Eight EXP Microwave System
    • Using a Biotage Initiator Eight EXP Microwave System.
  • 84
    • 58549117410 scopus 로고    scopus 로고
    • Initially when the Pd2(dba)3-ligand solutions were prepared they took on a dark red colour. After sufficient stirring they gradually changed to a bright yellow, indicating generation of the active form. When making larger stock solutions we observed that the activation times could be significantly longer with significant amounts of palladium black precipitating in the process. We later found that the activation times were improved by exposing as much of the surface area of the solution as possible to air while stirring vigorously. The palladium black can simply be filtered from the solution or allowed to settle to the bottom of the container, while the solution is taken from the surface. We later discovered that by doubling the number of equivalents of ligand, the palladium black precipitate was eliminated from the stock solution
    • 3-ligand solutions were prepared they took on a dark red colour. After sufficient stirring they gradually changed to a bright yellow, indicating generation of the active form. When making larger stock solutions we observed that the activation times could be significantly longer with significant amounts of palladium black precipitating in the process. We later found that the activation times were improved by exposing as much of the surface area of the solution as possible to air while stirring vigorously. The palladium black can simply be filtered from the solution or allowed to settle to the bottom of the container, while the solution is taken from the surface. We later discovered that by doubling the number of equivalents of ligand, the palladium black precipitate was eliminated from the stock solution.


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