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Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes.

Melcher, Michaela LU ; von Wachenfeldt, Henrik LU ; Sundin, Anders LU and Strand, Daniel LU (2015) In Chemistry: A European Journal 21(2). p.531-535
Abstract
Third-row transition metal catalysts remain a largely untapped resource in cycloaddition reactions for the formation of medium-sized rings. Herein, we report the first examples of iridium-catalyzed inter- and intramolecular vinylcyclopropane (VCP)-alkyne (5+2) cycloadditions. DFT modeling suggests that catalysis by iridium(I) proceeds through a mechanism similar to that previously reported for rhodium(I)-catalyzed VCP-alkyne cycloadditions, but a smaller free energy span for iridium enables substantially faster catalysis under favorable conditions. The system is characterized by up to quantitative yields and is amenable to an array of disubstituted alkynes and vinylcyclopropanes.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemistry: A European Journal
volume
21
issue
2
pages
531 - 535
publisher
Wiley-Blackwell
external identifiers
  • pmid:25413863
  • wos:000347231300004
  • scopus:84920201267
  • pmid:25413863
ISSN
1521-3765
DOI
10.1002/chem.201405729
language
English
LU publication?
yes
id
d755f2d5-f6f8-41aa-9e7a-f0aee16b9605 (old id 4816362)
date added to LUP
2016-04-01 09:53:21
date last changed
2022-08-27 03:39:14
@article{d755f2d5-f6f8-41aa-9e7a-f0aee16b9605,
  abstract     = {{Third-row transition metal catalysts remain a largely untapped resource in cycloaddition reactions for the formation of medium-sized rings. Herein, we report the first examples of iridium-catalyzed inter- and intramolecular vinylcyclopropane (VCP)-alkyne (5+2) cycloadditions. DFT modeling suggests that catalysis by iridium(I) proceeds through a mechanism similar to that previously reported for rhodium(I)-catalyzed VCP-alkyne cycloadditions, but a smaller free energy span for iridium enables substantially faster catalysis under favorable conditions. The system is characterized by up to quantitative yields and is amenable to an array of disubstituted alkynes and vinylcyclopropanes.}},
  author       = {{Melcher, Michaela and von Wachenfeldt, Henrik and Sundin, Anders and Strand, Daniel}},
  issn         = {{1521-3765}},
  language     = {{eng}},
  number       = {{2}},
  pages        = {{531--535}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry: A European Journal}},
  title        = {{Iridium Catalyzed Carbocyclizations: Efficient (5+2) Cycloadditions of Vinylcyclopropanes and Alkynes.}},
  url          = {{http://dx.doi.org/10.1002/chem.201405729}},
  doi          = {{10.1002/chem.201405729}},
  volume       = {{21}},
  year         = {{2015}},
}