Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols was written by Nacsa, Eric D.;MacMillan, David W. C.. And the article was included in Journal of the American Chemical Society in 2018.COA of Formula: C11H16O3 This article mentions the following:
Nature routinely engages alcs. as leaving groups, as DNA biosynthesis relies on the removal of water from ribonucleoside diphosphates by a radical-mediated “spin-center shift” (SCS) mechanism. Alcs., however, remain underused as alkylating agents in synthetic chem. due to their low reactivity in two-electron pathways. We report herein an enantioselective α-benzylation of aldehydes using alcs. as alkylating agents based on the mechanistic principle of spin-center shift. This strategy harnesses the dual activation modes of photoredox and organocatalysis, engaging the alc. by SCS and capturing the resulting benzylic radical with a catalytically generated enamine. Mechanistic studies provide evidence for SCS as a key elementary step, identify the origins of competing reactions, and enable improvements in chemoselectivity by rational photocatalyst design. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3COA of Formula: C11H16O3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.COA of Formula: C11H16O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem