Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates

Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2021, Volume: 64, Article number : 152737, Pages count : DOI: 10.1016/j.tetlet.2020.152737

Authors

Mulina Olga M. ¹ , Ilovaisky Alexey I. ^1,2 , Opatz Till ³ , Terent'ev Alexander O. ^1,2

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
2	All Russian Research Institute for Phytopathology, B. Vyazyomy, 143050 Moscow Region, Russian Federation
3	Department of Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.

Mulina O.M. , Ilovaisky A.I. , Opatz T. , Terent'ev A.O.
Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Tetrahedron Letters. 2021. V.64. 152737 . DOI: 10.1016/j.tetlet.2020.152737 WOS Scopus OpenAlex

Web of science:	WOS:000610242900011
Scopus:	2-s2.0-85098872962
OpenAlex:	W3119322883

DB	Citing
OpenAlex	19
Scopus	17
Web of science	17