Recent Advances in Cross-Dehydrogenative-Coupling Reactions Using Molecular Oxygen as the Sole Oxidant

doi:10.6023/cjoc202007007

Abstract

Cross-dehydrogenative-coupling (CDC) reactions have emerged as one of the most efficient and straightforward methods for the formation of C—C bonds or C-heteroatom bonds. However, most CDC reactions require hazardous and stoichiometric oxidants, such as PhI(OAc)₂, benzoquinone, copper(II) salts, organic peroxide acid and silver(I) salts. A green and environmentary benign approach is using molecular oxygen (O₂) as oxidant in the reactions, which usually form water as by-product. According to the classification of catalysts, the research progress of cross dehydrogenation coupling reaction with oxygen as the only oxidant is reviewed.

Key words: cross-dehydrogenative-coupling, molecular oxygen, oxidant

Cite this article

Weihui Zhuang, Xiaofeng Zhang, Qiufeng Huang. Recent Advances in Cross-Dehydrogenative-Coupling Reactions Using Molecular Oxygen as the Sole Oxidant[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 529-542.

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Fig. & Tab. 12

Scheme 1. Cross-dehydrogenative-coupling reactions using molecular oxygen as the sole oxidant

Scheme 2. Proposed mechanism of PdII-catalyzed cross-dehydrogenative-coupling using O2 as the oxidant

Scheme 3. Pd(II)-catalyzed olefination of electron-deficient arenes

Scheme 4. Mono-N-protected amino acid ligands accelerated palladium-catalyzed olefination of electron-deficient (hetero)arenes

Scheme 5. Palladium-catalyzed olefination and arylation of polyfluoroarenes using molecular oxygen as the sole oxidant

Scheme 6. Palladium-catalyzed C—H olefination of uracils and caffeines using molecular oxygen as the sole oxidant

Scheme 7. Palladium-catalyzed C—H arylation of uracils and caffeines using molecular oxygen as the sole oxidant

Scheme 8. Palladium-catalyzed bisolefination of C≡C triple bonds

Scheme 9. Iron-catalyzed oxidative C—C and N—N coupling of diarylamines

Scheme 10. Copper-catalyzed aerobic oxidative coupling of amines and phosphonates

Scheme 11. Mesoporous manganese oxide catalyzed oxidative coupling of anilines

Scheme 12. Catalyst-free cross-dehydrogenative coupling between xanthene derivatives and thiophenols

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