Repozytorium
Wyszukaj
Kolekcje
Inne
Direct synthesis of butadiynyl-substituted pyrroles under solvent- and transition metal-free conditions.
Autorzy
Rok wydania
2015
Czasopismo
Numer woluminu
5
Strony
73241-73248
DOI
10.1039/c5ra08820h
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The work describes a convenient and highly efficient C–H butadiynylation of substituted pyrroles with the use of 1-halobutadiynes. The method requires only a simple grinding of substrates in a mortar under mild, solvent- and transition metal-free conditions and constitutes the first example of pyrrole butadiynylation via cross-coupling reaction with the use of 1-halobutadiynes. The scope of this mechanochemical approach covers 4,5,6,7-tetrahydro-1H-indole, its N-substituted derivatives and 2-phenylpyrrole and on the other hand ester and phenyl end-capped 1-halobutadiynes including chlorides, bromides and iodides. Interestingly, the method has proven effective also for weak electron withdrawing aryl substituted 1-halobutadiynes what has not been yet achieved for 1-haloacetylenes. Such reactivity was unexpected in the view of the literature data and opened a gate to the plethora of substrates for organic synthesis including syntheses of pharmaceuticals. An X-ray analysis of two coupling products is also presented.
Adres publiczny
http://dx.doi.org/10.1039/c5ra08820h
Strona internetowa wydawcy
Podobne publikacje
Boric acid as an efficient and green catalyst for the synthesis of 2-amino-4,6-diarylnicotinonitrile under microwave irradiation in solvent-free conditions.
Hosseinzadeh Zahra, Ramazani Ali, Razzaghi-Asl Nima, Ślepokura Katarzyna, Lis Tadeusz
Perlite-SO3H nanoparticles as an efficient and reusable catalyst for one-pot three-component synthesis of 1,2-dihydro-1-aryl-naphtho[1,2-e][1,3]oxazine-3-one derivatives under both microwave-assisted and thermal solvent-free conditions : single crystal X-ray structure analysis and theoretical study.
Ramazani Ali, Rouhani Morteza, Mirhadi E., Sheikhi Masoome, Ślepokura Katarzyna, Lis Tadeusz