P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent was written by Bao, Hanyang;Zhou, Bingwei;Luo, Shu-Ping;Xu, Zheng;Jin, Hongwei;Liu, Yunkui. And the article was included in ACS Catalysis in 2020.Electric Literature of C8H5IS This article mentions the following:
A deoxygenative radical alkylation of aromatic alkynes with alkyl aldehydes for the preparation of allylarenes was successfully achieved. This transformation is accomplished through the reaction of alkyl aldehydes with alkynes in the presence of dipropylamine and Hantzsch ester catalyzed by a P/N heteroleptic Cu(I)-based photosensitizer under photoredox catalysis conditions. Preliminary mechanistic studies reveal that this aldehyde-alkyne coupling process comprises a regioselective radical addition of in-situ-generated alkyl-substituted α-amino radicals to alkynes with subsequent 1,5-proton transfer, C-N bond cleavage and concomitant isomerization of the resulting allyl radical species. Thus, in net result, dipropylamine serves as a traceless linker agent for the deoxygenative radical cross-coupling of alkyl aldehydes with alkynes under photoredox catalysis reaction conditions. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Electric Literature of C8H5IS).
3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond.Electric Literature of C8H5IS
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com