Full Cleavage of C C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine

Full Cleavage of C C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine Full article

Journal

Australian Journal of Chemistry
ISSN: 0004-9425 , E-ISSN: 1445-0038

Output data

Year: 2017, Volume: 70, Number: 4, Pages: 421-429 Pages count : 9 DOI: 10.1071/CH17026

Authors

Vasilevsky Sergei F. ¹ , Davydova Maria P. ¹ , Mamatyuk Victor I. ² , Tsvetkov Nikolay ³ , Hughes Audrey ³ , Baranov Denis S. ¹ , Alabugin Igor V. ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, Voevodsky Inst Chem Kinet & Combust, Siberian Branch, 3 Inst Skaya St, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.

Vasilevsky S.F. , Davydova M.P. , Mamatyuk V.I. , Tsvetkov N. , Hughes A. , Baranov D.S. , Alabugin I.V.
Full Cleavage of C C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine
Australian Journal of Chemistry. 2017. V.70. N4. P.421-429. DOI: 10.1071/CH17026 WOS Scopus OpenAlex

Web of science:	WOS:000398533900010
Scopus:	2-s2.0-85016809022
OpenAlex:	W2592711852

DB	Citing
Web of science	16
Scopus	13
OpenAlex	16