scholarly journals Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

2013 ◽  
Vol 9 ◽  
pp. 1713-1717 ◽  
Author(s):  
Daisuke Hirose ◽  
Tsuyoshi Taniguchi
Keyword(s):  
Molecular Oxygen ◽  
Hydrogen Shift ◽  
Tert Butyl

Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.

Palladium-Catalyzed C(sp3)–H Nitrooxylation with tert-Butyl Nitrite and Molecular Oxygen

2020 ◽  
Vol 22 (24) ◽  
pp. 9719-9723
Author(s):  
Bo Li ◽  
Ye-Qiang Han ◽  
Xu Yang ◽  
Bing-Feng Shi
Keyword(s):  
Molecular Oxygen ◽  
Tert Butyl ◽  
Palladium Catalyzed

tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis

Synthesis ◽  
2017 ◽  
Vol 50 (04) ◽  
pp. 711-722 ◽  
Author(s):  
Xiaodong Jia ◽  
Pengfei Li
Keyword(s):  
Molecular Oxygen ◽  
Organic Synthesis ◽  
Radical Reactions ◽  
Organic Transformations ◽  
Metal Free ◽  
Tert Butyl ◽  
The Past ◽  
Recent Advances ◽  
Versatile Reagent

tert-Butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations. Besides its traditional applications in nitrosation and diazotization, its ability to activate molecular oxygen to enable the initiation of radical reactions, including nitration, oximation, oxidation, and so on, has attracted extensively attention in the past decade. This review highlights recent advances in this field to promote further exploration of this versatile compound.1 Introduction2 Reactions Involving TBN2.1 Nitrosation2.2 Oximation2.3 Diazotization2.4 Nitration2.5 Oxidation2.6 Other Reactions3 Conclusion and Perspective

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