Radical Carbonyl Umpolung Arylation via Dual Catalysis was written by Huang, Huan-Ming;Bellotti, Peter;Erchinger, Johannes E.;Paulisch, Tiffany O.;Glorius, Frank. And the article was included in Journal of the American Chemical Society in 2022.Safety of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:
A series of aryl benzoates I [R = iPr, tBu, cyclohexyl, etc.; R1 = 4-NCC6H4, 2-NCC6H4, 2-pyridyl, etc.] via dual nickel and photoredox catalyzed radical carbonyl umpolung arylation of aldehydes and aryl bromides was reported. This redox-neutral approach provided a complementary method to construct Grignard-type products from (hetero)aryl bromides and aliphatic aldehydes, without the need for prefunctionalization. Sequential activation, hydrogen atom transfer and halogen atom transfer process could directly converted aldehydes to the corresponding ketyl radicals, which further react with aryl-nickel intermediates in an overall polarity-reversal process. This radical strategy tolerated-among others-acidic functional groups, heteroaryl motifs and sterically hindered substrates and was applied in the late-stage modification of drugs and natural products. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Safety of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Safety of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts