A cross-dehydrogenative C(sp3)−H heteroarylation via photo-induced catalytic chlorine radical generation

Hydrogen atom abstraction (HAT) from C( sp 3 )–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs since involving stoichiometric oxidants, excessive alkane loading, and limited scope are common drawb...

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Vydané v:Nature communications Ročník 12; číslo 1; s. 4010 - 9
Hlavní autori: Huang, Chia-Yu, Li, Jianbin, Li, Chao-Jun
Médium: Journal Article
Jazyk:English
Vydavateľské údaje: London Nature Publishing Group UK 29.06.2021
Nature Publishing Group
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Predmet:
639/638/549/933
639/638/77/888
Alkanes
Alkylation
Catalysts
Chemistry
Chlorides
Chlorine
Cobalt
Couplings
Dehydrogenation
Design
Humanities and Social Sciences
Hydrogen
Hydrogen bonds
Hydrogen evolution
Ligands
multidisciplinary
Oxidants
Oxidation
Oxidizing agents
Radicals
Science
Science (multidisciplinary)
Solvents
Substrates
ISSN:2041-1723, 2041-1723
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Shrnutí:Hydrogen atom abstraction (HAT) from C( sp 3 )–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs since involving stoichiometric oxidants, excessive alkane loading, and limited scope are common drawbacks. Here we report a photo-induced and chemical oxidant-free cross-dehydrogenative coupling (CDC) between alkanes and heteroarenes using catalytic chloride and cobalt catalyst. Couplings of strong C( sp 3 )–H bond-containing substrates and complex heteroarenes, have been achieved with satisfactory yields. This dual catalytic platform features the in situ engendered chlorine radical for alkyl radical generation and exploits the cobaloxime catalyst to enable the hydrogen evolution for catalytic turnover. The practical value of this protocol was demonstrated by the gram-scale synthesis of alkylated heteroarene with merely 3 equiv. alkane loading. Hydrogen atom abstraction from C( sp 3 )–H bonds of naturally abundant alkanes for alkyl radical generation represents a promising yet underexplored strategy in the alkylation reaction designs. Here the authors show a photo-induced and chemical oxidant-free cross-dehydrogenative coupling between alkanes and heteroarenes using catalytic chloride and cobalt catalyst.
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ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-021-24280-9