Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHCBH₃). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHCBH₂Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono- and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.

A new approach for synthesis of fawcettimine-type Lycopodium alkaloids is described. A divergent strategy was achieved by applying stereoselective Diels–Alder reaction followed by redox-controlled elaboration. Eventually, (−)-8-deoxyserratinine, (+)-fawcettimine, (−)-lycopoclavamine-A, (−)-serratine, (−)-lycopoclavamine-B and (−)-serratanidine were successfully accessed.

Arynes were generated in situ from ortho-silyl aryl triflates and fluoride ions in the presence of stable N-heterocyclic carbene boranes (NHCBH₃). Spontaneous hydroboration ensued to provide stable B-aryl-substituted NHC-boranes (NHCBH₂Ar). The reaction shows good scope in terms of both the NHC-borane and aryne components and provides direct access to mono- and disubstituted NHC-boranes. The formation of unusual ortho regioisomers in the hydroboration of arynes with an electron-withdrawing group supports a hydroboration process with hydride-transfer character.

Various 1,4-diols are easily accessible from alkenes through iron-catalyzed aerobic hydration. The reaction system consists of a user-friendly iron phthalocyanine complex, sodium borohydride, and molecular oxygen. Furthermore, the effect of additional ligands on the iron complex was examined for a model reaction. The second hydroxy group is installed by direct C(sp³)H oxygenation, which is based on a [1,5] hydrogen shift process of a transient alkoxy radical that is formed by formal hydration of the olefin.

Various 1,4-diols are easily accessible from alkenes through iron-catalyzed aerobic hydration. The reaction system consists of a user-friendly iron phthalocyanine complex, sodium borohydride, and molecular oxygen. Furthermore, the effect of additional ligands on the iron complex was examined for a model reaction. The second hydroxy group is installed by direct C(sp³)H oxygenation, which is based on a [1,5] hydrogen shift process of a transient alkoxy radical that is formed by formal hydration of the olefin.

A method for the oxidative nitration of alkenes using a combination of tert-butyl nitrite and molecular oxygen to give β-nitro alcohols and their nitrate derivatives has been developed. The present reaction provides a practical method for the synthesis of nitro compounds because of the mild reaction conditions, the use of inexpensive reagents and a simple experimental procedure.

A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassium ferrocyanide trihydrate (K₄[Fe(CN)₆]⋅3 H₂O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions were achieved at room temperature in the presence of iron catalyst, oxygen gas, and water. A method involving aniline as a radical precursor is also described.