Cart
Communication
Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides
Full Text HTML
Hi-Res PDFPurchase the full-text
- PDF/HTML,
figures/images,
references and tables,
(where available)
Section:Abstract
Ni-catalyzed Sonogashira coupling of nonactivated, β-H-containing alkyl halides, including chlorides, is reported. The coupling is tolerant to a wide range of functional groups, including ether, ester, amide, nitrile, keto, heterocycle, acetal, and aryl halide, in both coupling partners. The coupling can be selective for a specific C−X bond (X = I, Br, Cl) and allows for orthogonal functionalization of alkyl halides with multiple reactive sites.
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 5 ACS Journal articles (5 most recent appear below).
Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492
Why Are (NN2)Ni Pincer Complexes Active for Alkyl−Alkyl Coupling: β-H Elimination Is Kinetically Accessible but Thermodynamically Uphill
Jan Breitenfeld, Oleg Vechorkin, Clémence Corminboeuf, Rosario Scopelliti and Xile HuOrganometallics2010 29 (17), 3686-3689Why Are (NN2)Ni Pincer Complexes Active for Alkyl−Alkyl Coupling: β-H Elimination Is Kinetically Accessible but Thermodynamically Uphill
Jan Breitenfeld, Oleg Vechorkin, Clémence Corminboeuf, Rosario Scopelliti and Xile HuOrganometallics2010 29 (17), 3686-3689Isomerization and olefin exchange experiments show that β-H elimination is kinetically viable but thermodynamically unfavorable in [(MeNN2)Ni-alkyl] complexes. The intermediacy of Ni-hydride species was corroborated by a trapping experiment. The alkyl ...
Copper(I) Iodide Polyphosphine Adducts at Low Loading for Sonogashira Alkynylation of Demanding Halide Substrates: Ligand Exchange Study between Copper and Palladium
Matthieu Beaupérin, Andre Job, Hélène Cattey, Sylviane Royer, Philippe Meunier and Jean-Cyrille HiersoOrganometallics2010 29 (12), 2815-2822Copper(I) Iodide Polyphosphine Adducts at Low Loading for Sonogashira Alkynylation of Demanding Halide Substrates: Ligand Exchange Study between Copper and Palladium
Matthieu Beaupérin, Andre Job, Hélène Cattey, Sylviane Royer, Philippe Meunier and Jean-Cyrille HiersoOrganometallics2010 29 (12), 2815-2822The prestabilization of copper iodide with a multidentate ferrocenyl phosphine ligand promotes the palladium-catalyzed cross-coupling of demanding halides with phenylacetylene in a selective way. Novel CuI-triphosphine adducts are described in the solid ...
Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles
Maddali L. N. Rao, Deepak N. Jadhav and Priyabrata DasguptaOrganic Letters2010 12 (9), 2048-2051Pd-Catalyzed Domino Synthesis of Internal Alkynes Using Triarylbismuths as Multicoupling Organometallic Nucleophiles
Maddali L. N. Rao, Deepak N. Jadhav and Priyabrata DasguptaOrganic Letters2010 12 (9), 2048-2051The domino coupling reaction of 1,1-dibromo-1-alkenes with triarylbismuth nucleophiles has been demonstrated to furnish disubstituted alkynes directly under catalytic palladium conditions. The couplings of triarylbismuths as multicoupling nucleophiles ...
Negishi Alkyl−Aryl Cross-Coupling Catalyzed by Rh: Efficiency of Novel Tripodal 3-Diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl Acetate Ligand
Syogo Ejiri, Shunsuke Odo, Hideki Takahashi, Yugo Nishimura, Kazuma Gotoh, Yasushi Nishihara and Kentaro TakagiOrganic Letters2010 12 (8), 1692-1695Negishi Alkyl−Aryl Cross-Coupling Catalyzed by Rh: Efficiency of Novel Tripodal 3-Diphenylphosphino-2-(diphenylphosphino)methyl-2-methylpropyl Acetate Ligand
Syogo Ejiri, Shunsuke Odo, Hideki Takahashi, Yugo Nishimura, Kazuma Gotoh, Yasushi Nishihara and Kentaro TakagiOrganic Letters2010 12 (8), 1692-16953-Diphenylphosphino-2-(diphenylphoshino)methyl-2-methylpropyl acetate acted as an efficient ligand for a Rh catalyst, achieving cross-coupling between arylzinc compounds bearing electron-withdrawing groups and alkyl electrophiles. The beneficial effect ...
Tools
-
Add to Favorites
-
Download Citation
-
Email a Colleague -
Permalink
Order Reprints
Rights & Permissions
Citation Alerts
History
- Published In Issue September 02, 2009
- Article ASAPAugust 11, 2009
- Received: July 20, 2009
ACS
Network
Facebook
Tweet This
CiteULike
Newsvine
Digg This
Delicious
