Cart
Article
Cobalt-Catalyzed Reductive Coupling of Activated Alkenes with Alkynes
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
Cobalt complex/Zn systems effectively catalyze the reductive coupling of activated alkenes with alkynes in the presence of water to give substituted alkenes with very high regio- and stereoselectivity in excellent yields. While the intermolecular reaction of acrylates, acrylonitriles, and vinyl sulfones with alkynes takes place in the presence of CoI2(PPh3)2/Zn, the reaction of enones and enals with alkynes requires the use of the CoI2(dppe)/Zn/ZnI2 system. The intramolecular reductive coupling of activated alkenes (enones, enals, acrylates, and acrylonitriles) with alkynes also works efficiently. Further a variety of cyclic lactones and lactams were prepared using this methodology. Possible mechanistic pathways are proposed based on a deuterium-labeling experiment carried out in the presence of D2O.
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 14 ACS Journal articles (5 most recent appear below).
Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes
Masato Ohashi, Tomoaki Taniguchi, and Sensuke OgoshiJournal of the American Chemical Society2011 Article ASAPNickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes
Masato Ohashi, Tomoaki Taniguchi, and Sensuke OgoshiJournal of the American Chemical Society2011 Article ASAPOxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C–O ...
Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
Aireal D. Jenkins, Ananda Herath, Minsoo Song, and John MontgomeryJournal of the American Chemical Society2011 Article ASAPSynthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
Aireal D. Jenkins, Ananda Herath, Minsoo Song, and John MontgomeryJournal of the American Chemical Society2011 Article ASAPStrategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal–alkyne cycloaddition directly affords cyclopentenols, whereas the enoate–alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of ...
Direct Michael Addition of Alkenes via a Cobalt-Dinitrosyl Mediated Vinylic C–H Functionalization Reaction
Chen Zhao, F. Dean Toste, and Robert G. BergmanJournal of the American Chemical Society2011 133 (28), 10787-10789Direct Michael Addition of Alkenes via a Cobalt-Dinitrosyl Mediated Vinylic C–H Functionalization Reaction
Chen Zhao, F. Dean Toste, and Robert G. BergmanJournal of the American Chemical Society2011 133 (28), 10787-10789We report a one-pot, direct C–H functionalization reaction of alkenes mediated by [CpCo(NO)2]. All intermediates in the proposed reaction sequence have been characterized. A variety of Michael acceptors can be utilized with the one-pot procedure to give ...
Enone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles
Benjamin B. Thompson and John MontgomeryOrganic Letters2011 13 (13), 3289-3291Enone–Alkyne Reductive Coupling: A Versatile Entry to Substituted Pyrroles
Benjamin B. Thompson and John MontgomeryOrganic Letters2011 13 (13), 3289-3291The reductive coupling of enones or enals with alkynes, followed by olefin oxidative cleavage and Paal–Knorr cyclization, provides a versatile entry to a variety of pyrrole frameworks. A number of limitations of alternate entries to the requisite 1,4-...
Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
Chu-Hung Wei, Subramaniyan Mannathan, and Chien-Hong ChengJournal of the American Chemical Society2011 133 (18), 6942-6944Enantioselective Synthesis of β-Substituted Cyclic Ketones via Cobalt-Catalyzed Asymmetric Reductive Coupling of Alkynes with Alkenes
Chu-Hung Wei, Subramaniyan Mannathan, and Chien-Hong ChengJournal of the American Chemical Society2011 133 (18), 6942-6944A CoI2/(R)-BINAP, Zn, ZnI2, H2O system efficiently catalyzes the intermolecular asymmetric reductive coupling of alkynes with cyclic enones to afford highly regio- and enantioselective β-alkenyl cyclic ketones. A possible mechanism that involves the ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue October 03, 2007
- Received May 19, 2007
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
