UV‐Induced C−H Functionalization of Alkanes with NO2 in Supercritical Carbon Dioxide

UV‐Induced C−H Functionalization of Alkanes with NO2 in Supercritical Carbon Dioxide Full article

Journal

ChemPhotoChem
ISSN: 2367-0932

Output data

Year: 2022, Volume: 6, Number: 8, Article number : e202200084, Pages count : DOI: 10.1002/cptc.202200084

Authors

Ivanov Roman E. ¹ , Zharkov Mikhail N. ¹ , Zlotin Sergei G. ¹

Affiliations

1	I. N. Nazarov Laboratory of Fine Organic Synthesis, N.D. Zelinsky Institute of organic chemistry Russian academy of sciences, Leninsky Prospect, 47, Moscow, 119991 Russia

A novel catalyst-free method for functionalization of unbranched alkanes via radical nitration with UV-activated nitrogen oxide (IV) in supercritical carbon dioxide medium has been developed. The method allows to transform these inactive substrates into corresponding nitrates and nitro compounds with outstanding yields (up to 65 %), using available reagents (NO2, O2) under mild reaction conditions (35–50 °C), and exhibits lower hazards compared to conventional analogues. An improved selectivity towards the nitrates has been achieved by adding pure oxygen to the reaction. Based on changes in reaction rate and product composition, the plausible reaction mechanism for the UV-induced C−H functionalization of alkanes with nitrogen oxide (IV) and pure oxygen has been proposed.

Ivanov R.E. , Zharkov M.N. , Zlotin S.G.
UV‐Induced C−H Functionalization of Alkanes with NO2 in Supercritical Carbon Dioxide
ChemPhotoChem. 2022. V.6. N8. e202200084 . DOI: 10.1002/cptc.202200084 WOS Scopus OpenAlex

Web of science:	WOS:000798998700001
Scopus:	2-s2.0-85130401084
OpenAlex:	W4229363586

DB	Citing
OpenAlex	12
Scopus	12
Web of science	11