- Dibromo-BODIPY as an Organic Photocatalyst for Radical-Ionic Sequences
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A new dibrominated 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is reported as a new metal-free photocatalyst. This BODIPY showed similar optoelectronic, electrochemical, and performance properties to those of Ru(bpy)3Cl2, one of the most common photocatalysts in a known radical-ionic transformation, such as the formation of 1,4-dicarbonyl compounds. Moreover, additional sequences in which the generated oxonium ion is trapped by an internal nucleophile were developed using this BODIPY photocatalyst. These new sequences allowed the straightforward preparation of ?3-alkoxylactones, monoprotected 1,4-ketoaldehydes, and dihydrofurans. This new catalyst, the methodology, and the forged functional groups could be important tools in organic synthesis.
- Garciá-Santos, William H.,Ordó?ez-Hernández, Javier,Farfán-Paredes, Mónica,Castro-Cruz, Hiram M.,Maciás-Ruvalcaba, Norma A.,Farfán, Norberto,Cordero-Vargas, Alejandro
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p. 16315 - 16326
(2021/11/18)
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- The complete stereochemistry of the enzymatic dehydration of 4-hydroxybutyryl coenzyme A to crotonyl coenzyme A
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(Chemical Equation Presented) The stereospecific action of the microbial enzyme 4-hydroxybutyryl-CoA dehydratase on the three prochiral centers of its substrate 4-hydroxybutyryl-CoA can now be described as anti elimination of the 2Re and 3Si hydrogen atoms with retention of configuration during the substitution of the hydroxy group by a hydrogen atom. The results confirm the relationship of the dehydratase to acyl-CoA dehydrogenases and the view that the Fe4S4 cluster acts as a Lewis acid.
- Friedrich, Peter,Darley, Daniel J.,Golding, Bernard T.,Buckel, Wolfgang
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p. 3254 - 3257
(2008/12/23)
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- STANNYL ESTER CYCLIZATIONS
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Alpha halo stannyl esters react with alkenes to afford lactones.The reaction is catalyzed by AIBN.The reaction proceeds best with electron rich alkenes.The mechanistic aspects of this novel reaction are discussed.This reaction can also be conducted intramolecularly to produce bicyclic lactones.An approach to the lignan system is presented.
- Kraus, George A.,Landgrebe, Kevin
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p. 4039 - 4046
(2007/10/02)
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- THE TRANSFORMATION OF ALKENES INTO γ-LACTONES USING α-IODOESTERS
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Iodostannyl esters react with alkenes in the presence of AIBN to afford γ-lactones.
- Kraus, George A.,Landgrebe, Kevin
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p. 3939 - 3942
(2007/10/02)
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