Dual Photochemical H-Atom Transfer and Cobalt Catalysis for the Desaturative Synthesis of Phenols from Cyclohexanones

被引:19
|
作者
Caldora, Henry P. [1 ]
Zhang, Zhenhua [1 ]
Tilby, Michael J. [1 ]
Turner, Oliver [2 ]
Leonori, Daniele [3 ]
机构
[1] Univ Manchester, Dept Chem, Oxford Rd, Manchester M13 9PL, England
[2] AstraZeneca, Unit 310, Oncol R&DI Med Chem, Darwin Bldg,Cambridge Sci Pk,Milton Rd, Cambridge CB4 0WG, England
[3] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52056 Aachen, Germany
关键词
Cobalt Catalysis; Desaturation; H-Atom Transfer; Phenols; ELECTROPHILIC AROMATIC-SUBSTITUTION; KETO-ENOL-TAUTOMERISM; AEROBIC DEHYDROGENATION; ORTHO-BORYLATION; ALKYLATION; NITRATION; ARENES; ALKYLCOBALOXIMES; OXIDATION; PRODUCTS;
D O I
10.1002/anie.202301656
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Phenols are integral aromatic molecules widely encountered in the structure of natural products and routinely utilised for the synthesis of high-value materials. Accessing highly substituted derivatives can often be difficult, especially when their functionalization pattern does not match the intrinsic reactivity leveraged by electrophilic aromatic substitution (SEAr) chemistry. Here, we provide an alternative and mechanistically distinct approach for phenol synthesis using saturated cyclohexanone precursors. This process operates at ambient temperature, under simple purple light irradiation, and features a dual catalytic manifold carrying four sequential H-atom transfer processes.
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页数:6
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