3978-81-2Relevant articles and documents
Generation of Functionalized Alkyl Radicals via the Direct Photoexcitation of 2,2′-(Pyridine-2,6-diyl)diphenol-Based Borates
Miyamoto, Yusuke,Sumida, Yuto,Ohmiya, Hirohisa
supporting information, p. 5865 - 5870 (2021/07/31)
A new type of alkylborate was developed for the purpose of generating radicals via direct photoexcitation. These borates were prepared using 2,2′-(pyridine-2,6-diyl)diphenol as a tridentate ligand together with organoboronic acids or potassium trifluoroborates. The ready availability of organoboron compounds is a significant advantage of this direct photoexcitation protocol. The excited states of these borates can also serve as strong reductants, enabling various transformations.
Clean protocol for deoxygenation of epoxides to alkenes: Via catalytic hydrogenation using gold
Fiorio, Jhonatan L.,Rossi, Liane M.
, p. 312 - 318 (2021/01/29)
The epoxidation of olefin as a strategy to protect carbon-carbon double bonds is a well-known procedure in organic synthesis, however the reverse reaction, deprotection/deoxygenation of epoxides is much less developed, despite its potential utility for the synthesis of substituted olefins. Here, we disclose a clean protocol for the selective deprotection of epoxides, by combining commercially available organophosphorus ligands and gold nanoparticles (Au NP). Besides being successfully applied in the deoxygenation of epoxides, the discovered catalytic system also enables the selective reduction N-oxides and sulfoxides using molecular hydrogen as reductant. The Au NP catalyst combined with triethylphosphite P(OEt)3 is remarkably more reactive than solely Au NPs. The method is not only a complementary Au-catalyzed reductive reaction under mild conditions, but also an effective procedure for selective reductions of a wide range of valuable molecules that would be either synthetically inconvenient or even difficult to access by alternative synthetic protocols or by using classical transition metal catalysts. This journal is
Generation of Alkyl Radical through Direct Excitation of Boracene-Based Alkylborate
Hashizume, Daisuke,Hosoya, Takamitsu,Nakamura, Kei,Ohmiya, Hirohisa,Sato, Yukiya,Sumida, Yuto
supporting information, p. 9938 - 9943 (2020/06/27)
The generation of tertiary, secondary, and primary alkyl radicals has been achieved by the direct visible-light excitation of a boracene-based alkylborate. This system is based on the photophysical properties of the organoboron molecule. The protocol is applicable to decyanoalkylation, Giese addition, and nickel-catalyzed carbon-carbon bond formations such as alkyl-aryl cross-coupling or vicinal alkylarylation of alkenes, enabling the introduction of various C(sp3) fragments to organic molecules.
