Journal article

Ligand bite angle-dependent palladium-catalyzed cyclization of propargylic carbonates to 2-alkynyl azacycles or cyclic dienamides.

Abstract:: The regioselectivity of the palladium-catalyzed cyclization of propargylic carbonates with sulfonamide nucleophiles is critically dependent on the bite angle of the bidentate phosphine ligand. Ligands with small bite angles favor attack on the central carbon atom of an allenylpalladium intermediate to afford cyclic dienamide products, whereas the use of those with large bite angles leads to alkynyl azacycles, with high stereoselectivity. A computational analysis of the reaction pathway is also presented.

Publication status:: Published

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APA Style

Daniels, D., Jones, A., Thompson, A., Paton, R., & Anderson, E. (2014). Ligand bite angle-dependent palladium-catalyzed cyclization of propargylic carbonates to 2-alkynyl azacycles or cyclic dienamides. Angewandte Chemie (International Ed. in English), 53(7), 1915–1920.

MLA Style

Daniels, D, et al. “Ligand Bite Angle-Dependent Palladium-Catalyzed Cyclization of Propargylic Carbonates to 2-Alkynyl Azacycles or Cyclic Dienamides.” Angewandte Chemie (International Ed. in English), vol. 53, no. 7, 2014, pp. 1915–20.

Chicago Style

Daniels, D, A Jones, A Thompson, R Paton, and E Anderson. 2014. “Ligand Bite Angle-Dependent Palladium-Catalyzed Cyclization of Propargylic Carbonates to 2-Alkynyl Azacycles or Cyclic Dienamides.” Angewandte Chemie (International Ed. in English) 53 (7): 1915–20.
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Publisher copy:: 10.1002/anie.201309162

Authors

+ Daniels, D More by this author

Role:: Author

+ Jones, A More by this author

Role:: Author

+ Thompson, A More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Inorganic Chemistry
Role:: Author

+ Paton, R More by this author

Role:: Author

+ Anderson, E More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

Journal:: Angewandte Chemie (International ed. in English) More from this journal
Volume:: 53
Issue:: 7
Pages:: 1915-1920
Publication date:: 2014-02-01
DOI:: 10.1002/anie.201309162
EISSN:: 1521-3773
ISSN:: 1433-7851

Language:: English
Keywords:: Cyclization

Catalysis

Alkynes

Carbonates

Palladium

Azo Compounds

Ligands

Molecular Structure

Acrylamides

Stereoisomerism
Pubs id:: pubs:447889
UUID:: uuid:160ac668-3d81-4fbd-a98e-beb688b533b6
Local pid:: pubs:447889
Source identifiers:: 447889
Deposit date:: 2014-02-13
ARK identifier:: ark:/29072/ora_160ac6683d814fbda98ebeb688b533b6

Terms of use

Copyright date:: 2014

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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