55836-65-2Relevant academic research and scientific papers
Evidence for direct hydride delivery from formic acid in transfer hydrogenation
Yu, Jinquan,Spencer, Jonathan B.
, p. 2237 - 2240 (1999)
The regioselectivity of hydrometalation in transfer hydrogenation was investigated by tracing the fate of the deuterium label in both the formyl and carboxyl positions of formic acid during the isomerization of a cis enol ether. The deuterium from the for
Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
Iakovenko, Roman,Hlavá?, Jan
supporting information, p. 440 - 446 (2021/01/28)
Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is
Cathodic reduction of N-(2-iodophenyl)-N-alkylcinnamides: A novel sequential electrochemical radical cyclisation and hydroxylation
Munusamy, Raja,Dhathathreyan, Kaveripatnam Samban,Balasubramanian, Kalpattu Kuppusamy,Venkatachalam, Chitoor Sivaramakrishnan
, p. 1154 - 1166 (2007/10/03)
In recent years, intramolecular aryl radical cyclisation has emerged as a useful route for the synthesis of benzannulated heterocycles and carbocycles. The aryl radicals are generated in situ from aryl halides (iodides or bromides) with tributylstannyl hydride-AIBN, SmI2, Co(I) or under photochemical conditions. The present work envisages the generation of aryl radicals by cathodic reduction of the carbon-iodine bond of N-(2-iodophenyl)-N-alkylcinnamides and their intramolecular cyclisation. The cathodic reduction of N-(2-iodophenyl)-N-alkyl-cinnamides under deaerated conditions in DMF gave 1-alkyl-3-benzylindolin-2-ones regioselectively and in the presence of oxygen yielded surprisingly 1-alkyl-3-hydroxy-3-benzylindolin-2-ones. Both these products were formed by a 5-exo-trig process in good yields. A mechanism for the formation of the products has been proposed through the use of cyclic voltammetry, coulometry and controlled-potential electrolysis as well as deuterium labelling.
Heterogeneous transfer hydrogenation involves pairwise hydrogen transfer from the same position of two molecules of formic acid
Yu, Jinquan,Spencer, Jonathan B.
, p. 1935 - 1936 (2007/10/03)
Using the reduction of an alkyne to cis-alkene as hydrogen trap, differentially deuterium labelled formic acid is shown to deliver a pair of hydrogen atoms either from the formyl or the carboxy position, which suggests that palladium diformate is a key intermediate in heterogeneous transfer hydrogenation.
