150171-95-2Relevant academic research and scientific papers
Nickel/Photo-Cocatalyzed C(sp2)-H Allylation of Aldehydes and Formamides
Fan, Pei,Wang, Rui,Wang, Chuan
supporting information, p. 7672 - 7677 (2021/10/12)
Herein we report a nickel/photo-cocatalyzed C(sp2)-H allylation of aldehydes and formamides wherein both allyl acetates and allyl alcohols can be used as the allylating agents. In this reaction, radical-type umpolung of the formyl moiety is enabled by tetrabutylammonium decatungstate as a hydrogen-atom-transfer photocatalyst, whereas nickel serves to cleave the C-O bond of allyl acetates or allyl alcohols. The synergistic effect of these two catalysts provides new access to various β,γ-unsaturated ketones and amides with high selectivities.
An amidyl radical cyclisation approach towards the synthesis of β-lactams
Clark, Andrew J.,Peacock, Joanne L.
, p. 1265 - 1268 (2007/10/03)
Amidyl radicals generated from tributylstannane mediated homolysis of O-benzoyl hydroxamic acid derivatives (2a-d) undergo 4-exo trig cyclisation to furnish β-lactam derivatives (4a-d).
Aza- and oxacarbonylations of allyl phosphates catalyzed by rhodium carbonyl cluster. Selective synthesis of β,γ-unsaturated amides, esters, and acids
Imada, Yasushi,Shibata, Ou,Murahashi, Shun-Ichi
, p. 183 - 194 (2007/10/02)
Rhodium-catalyzed carbonylation of allyl phosphates under CO (20 atm) at 50 deg C proceeds very efficiently in the presence of amines, alcohols, and water to give the corresponding β,γ-unsaturated amides, esters, and acids, respectively.These carbonylations occur with high regioselectivity at the less substituted carbon of allyl unit to give linear β,υ-unsaturated acid derivatives.
Photophysical and photochemical behavior of intramolecular-styrene-amine exciplexes
Lewis, Frederick D.,Dasharatha Reddy,Schneider, Siegfried,Ga, Michael
, p. 3498 - 3506 (2007/10/02)
The photophysical and photochemical behavior of a series of secondary and tertiary ω-(β-styryl)aminoalkanes with one to five methylenes separating the styryl and amino groups has been investigated and compared to the intermolecular reactions of 1-phenylpropene with secondary and tertiary amines. The tertiary styrylamines form fluorescent intramolecular exciplexes, but fail to undergo intramolecular addition reactions. Both the rate constant for exciplex formation and the stability of the exciplex are dependent upon the length of the polymethylene chain connecting the chromophores. The failure of the tertiary amine exciplexes to undergo intramolecular addition is attributed to an unfavorable exciplex geometry for α-C-H transfer to the styrene double bond. While the secondary styrylamines do not form fluorescent exciplexes, the dependence of the styrene singlet lifetime upon the polymethylene chain length is similar to that for the tertiary styrylamines. Intramolecular N-H addition to the styrene double bond results in the formation of two regioisomeric (α-phenyl and α-benzyl) cyclic amines of different ring size. The regioisomer of larger ring size is favored except in the case in which four methylenes separate the chromophores. The effects of polymethylene chain length, solvent polarity, temperature, and the bulk of the N-alkyl group upon product yields and ratios are discussed in terms of a mechanism involving singlet exciplex and biradical intermediates.
