Boryl Radical Addition to Multiple Bonds in Organic Synthesis

2019 ◽  
Vol 2019 (37) ◽  
pp. 6308-6319 ◽  
Author(s):  
Tsuyoshi Taniguchi
Keyword(s):  
Organic Synthesis ◽  
Radical Addition ◽  
Multiple Bonds

scholarly journals Photocatalytic Atom Transfer Radical Addition to Olefins Utilizing Novel Photocatalysts

Molecules ◽  
2019 ◽  
Vol 24 (9) ◽  
pp. 1644 ◽  
Author(s):  
Errika Voutyritsa ◽  
Ierasia Triandafillidi ◽  
Nikolaos V. Tzouras ◽  
Nikolaos F. Nikitas ◽  
Eleftherios K. Pefkianakis ◽  
...  
Keyword(s):  
Metal Complexes ◽  
Organic Synthesis ◽  
Alkyl Group ◽  
Radical Addition ◽  
Bidentate Ligand ◽  
Atom Transfer ◽  
Broad Scope ◽  
Atom Transfer Radical Addition ◽  
Terpyridine Ligands ◽  
Photocatalytic Reactions

Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields.

scholarly journals Semiconductors as sensitisers for the radical addition of tertiary amines to electron deficient alkenes

2003 ◽  
Vol 5 (3) ◽  
pp. 175-182 ◽  
Author(s):  
Siniša Marinković ◽  
Norbert Hoffmann
Keyword(s):  
Electron Transfer ◽  
Organic Synthesis ◽  
Radical Reaction ◽  
Heterogeneous Photocatalysis ◽  
Radical Addition ◽  
Point Of View ◽  
Tertiary Amines ◽  
Radical Intermediate ◽  
Radical Chain ◽  
High Yields

Using heterogeneous photocatalysis, the radical addition of tertiary amines with electron deficient alkenes can be performed in high yields (up to 98%) and high facial diastereoselectivity. The photochemical induced electron transfer process initiates the radical chain reaction and inorganic semiconductors likeTiO2and ZnS were used. According to the proposed mechanism, the reaction takes place at the surface of the semiconductor and the termination step results from an interfacial electron transfer from the conduction band to the oxoallyl radical intermediate. Frequently, semiconductors are used for the mineralisation of organic compounds in wastewater. However, in this case, they are used in organic synthesis. The process can be performed in a convenient way and is particularly interesting from the ecological and economical point of view. No previous functionalization of the tertiary amines is necessary for C − C bond formation. Further on, the amines are used both as reactant and as solvent. The excess is recycled by distillation and the inexpensive sensitiser can be easily removed by filtration. In this way, products of high interest for organic synthesis are obtained by a diastereoselective radical reaction.

Ruthenium-catalysed hydrosilylation of carbon–carbon multiple bonds

2016 ◽  
Vol 3 (10) ◽  
pp. 1337-1344 ◽  
Author(s):  
M. Zaranek ◽  
B. Marciniec ◽  
P. Pawluć
Keyword(s):  
Organic Synthesis ◽  
Multiple Bonds ◽  
Recent Advances

Recent advances in ruthenium-catalysed hydrosilylation of C–C multiple bonds and its application to organic synthesis are highlighted.

scholarly journals Et3B Induced Stereoselective Radical Addition of Ph3GeH to Carbon–Carbon Multiple Bonds and Its Application to Isomerization of Olefins

1990 ◽  
Vol 63 (8) ◽  
pp. 2268-2272 ◽  
Author(s):  
Kyoko Nozaki ◽  
Yoshifumi Ichinose ◽  
Kuni Wakamatsu ◽  
Koichiro Oshima ◽  
Kiitiro Utimoto
Keyword(s):  
Radical Addition ◽  
Multiple Bonds

scholarly journals Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

2020 ◽  
Vol 16 ◽  
pp. 502-508
Author(s):  
Goki Hirata ◽  
Yu Yamane ◽  
Naoya Tsubaki ◽  
Reina Hara ◽  
Takashi Nishikata
Keyword(s):  
Alkyl Radical ◽  
Copper Catalyst ◽  
Radical Reaction ◽  
Reaction System ◽  
Radical Addition ◽  
Terminal Alkyne ◽  
Multiple Bonds ◽  
Complex Molecules ◽  
Reaction Patterns ◽  
Tertiary Alkyl

A terminal alkyne is one of the most useful reactants for the synthesis of alkyne and alkene derivatives. Because an alkyne undergoes addition reaction at a C–C triple bond or cross-coupling at a terminal C–H bond. Combining those reaction patterns could realize a new reaction methodology to synthesize complex molecules including C–C multiple bonds. In this report, we found that the reaction of 3 equivalents of terminal alkyne 1 (aryl substituted alkyne) and an α-bromocarbonyl compound 2 (tertiary alkyl radical precursor) undergoes tandem alkyl radical addition/Sonogashira coupling to produce 1,3-enyne compound 3 possessing a quaternary carbon in the presence of a copper catalyst. Moreover, the reaction of α-bromocarbonyl compound 2 and an alkyne 4 possessing a carboxamide moiety undergoes tandem alkyl radical addition/C–H coupling to produce indolinone derivative 5.

1.9 Oxygen-Centered Radicals

2021 ◽  
Author(s):  
J. Zhang ◽  
D. Liu ◽  
Y. Chen
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Radical Addition ◽  
Hydrogen Atom Transfer ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Carbon Carbon Bonds ◽  
Induced Reaction

AbstractOxygen-centered radicals (R1O•) are reactive intermediates in organic synthesis, with versatile synthetic utilities in processes such as hydrogen-atom transfer (HAT), β-fragmentation, radical addition to unsaturated carbon–carbon bonds, and rearrangement reactions. In this review, we focus on recent advances in the generation and transformation of oxygen-centered radicals, including (alkyl-, α-oxo-, aryl-) carboxyl, alkoxyl, aminoxyl, phenoxyl, and vinyloxyl radicals, and compare the reactivity of oxygen-centered radicals under traditional reaction conditions with their reactivity under visible-light-induced reaction conditions.

Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon-Carbon Multiple Bonds

2000 ◽  
Vol 73 (9) ◽  
pp. 2159-2160 ◽  
Author(s):  
Hidenori Kinoshita ◽  
Hirotada Kakiya ◽  
Koichiro Oshima
Keyword(s):  
Radical Addition ◽  
Multiple Bonds

ChemInform Abstract: Trialkylmanganate Mediated Radical Addition of Triphenylgermane to Carbon-Carbon Multiple Bonds.

ChemInform ◽  
2000 ◽  
Vol 31 (51) ◽  
pp. no-no
Author(s):  
Hidenori Kinoshita ◽  
Hirotada Kakiya ◽  
Koichiro Oshima
Keyword(s):  
Radical Addition ◽  
Multiple Bonds
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