- Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides
-
nickel-catalyzed cross-electrophile coupling is disclosed in which a range of vinyl bromides were utilized as electrophiles with oxalates derived from α-hydroxy carbonyls as precursors to carbonyl radical coupling partners. This method is compatible with a broad range of functional groups, providing a complementary solution for the construction of β,γ-unsaturated carbonyl compounds.
- Tong, Weiqi,Wu, Fan,Ye, Cheng
-
-
- Ni-catalyzed reductive coupling of α-halocarbonyl derivatives with vinyl bromides
-
This work describes the vinylation of α-halo carbonyl compounds with vinyl bromides under Ni-catalyzed reductive coupling conditions. While aryl-conjugated vinyl bromides entail pyridine as the sole labile ligand, the alkyl-substituted vinyl bromides require both bipyridine and pyridine as the co-ligands.
- Qiu, Canbin,Yao, Ken,Zhang, Xinghua,Gong, Hegui
-
p. 11332 - 11335
(2016/12/18)
-
- Olefination of carbonyl compounds through reductive coupling of alkenylboronic acids and tosylhydrazones
-
The partners decide: The C-C bond-forming reductive cross-coupling of alkenylboronic acids and tosylhydrazones takes place under mild reaction conditions without the need of a metal catalyst, thus giving rise to olefination-type products (see scheme). The position of the double bond in the product is determined by the structure of the coupling partners. Copyright
- Perez-Aguilar, M. Carmen,Valdes, Carlos
-
supporting information; experimental part
p. 5953 - 5957
(2012/07/30)
-
- Radical allylation, vinylation, alkynylation, and phenylation reactions of α-halo carbonyl compounds with organoboron, organogallium, and organoindium reagents
-
Allylic gallium and indium reagents are found to mediate radical allylation reactions of α-iodo or α-bromo carbonyl compounds. Treatment of benzyl bromoacetate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane provided benzyl 4-pentenoate in excellent yield. Addition of water as a co-solvent improved the yields of allylated products. Allylic indium reagents are also useful and can replace the gallium reagents. A diallylborane reagent can allylate an α-iodo ester in good yield. Alkenylation reactions of α-halo carbonyl compounds with alkenylindium proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties and styryl groups were introduced by this method. The carbon-carbon double bond geometry of the alkenylindiums was retained during the alkenylation. Preparation of an alkenylindium via a hydroindation of 1-alkyne and subsequent radical alkenylation established an efficient one-pot strategy. Radical alkynylations and phenylations with organoindium reagents are disclosed herein.
- Takami, Kazuaki,Usugi, Shin-Ichi,Yorimitsu, Hideki,Oshima, Koichiro
-
p. 824 - 839
(2007/10/03)
-
- Radical reactions in esters with alkoxy functionality chemistry an unusual alcohol moiety hydrogen abstraction
-
Various geometrically pure (E)-alkenes have been synthesized by radical substitution of alcohol moieties generated via hydrogen abstraction within ethyl esters. These reactions occurred with high regioselectivity and gave a new access to 1-methyl-3-aryl-allyl esters.
- Yan, Ming-Chung,Jang, Yeong-Jiunn,Wu, Jhenyi,Lin, Yung-Feng,Yao, Ching-Fa
-
p. 3685 - 3687
(2007/10/03)
-
- Radical alkenylation of α-halo carbonyl compounds with alkenylindiums
-
(Chemical equation presented) Alkenylation reaction of α-halo carbonyl compounds with alkenylindiums proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties as well as a styryl group could be introduced by this metho
- Takami, Kazuaki,Yorimitsu, Hideki,Oshima, Koichiro
-
p. 4555 - 4558
(2007/10/03)
-
- Cobaloxime-Catalyzed Radical Alkyl-Styryl Cross Couplings
-
Cobaloxime-catalyzed radical alkyl-styryl cross couplings can be accomplished by visible light photolysis of various alkyl bromides + styrene + in-situ-generated CoII(dmgH)2py + Zn in refluxing CH3CN or refluxing 95percentEtOH.cobaloximes; radi
- Branchaud, Bruce P.,Detlefsen, William D.
-
p. 6273 - 6276
(2007/10/02)
-
- Cobalt-Mediated Intermolecular Radical Additions to Carbon-to-Carbon Double Bonds leading to New Functionalised Alkenes
-
Alkyl radicals generated by photolytic homolysis of cobalt salophen reagents, e.g. (6) and (15), are shown to add to activated carbon-to-carbon double bonds, i.e. ethyl acrylate, methyl vinyl ketone, acrylonitrile, and styrene, producing preparatively useful yields of new alkene products, viz. (9), (10), (12) and (14) , and (16) .The reactions proceed via radical (Michael) additions, followed by 'dehydrocobaltation' from the presumed organocobalt intermediates (2) (Scheme 4).By use of this chemistry, in combination with the Schrauzer 'hydrocobaltation' reaction of alkenes, a new method for the cross-coupling reactions between two alkenes, leading to new functionalised alkenes, e.g. (24), (25), (26), (27), (28), and (29), is developed .
- Bhandal, Harcharan,Howell, Amy R.,Patel, Vinod F.,Pattenden, Gerald
-
p. 2709 - 2714
(2007/10/02)
-