Pyrrole synthesis using a tandem Grubbs' carbene-RuCl3 catalytic system
A straightforward pyrrole synthesis from diallylamines is developed by using a tandem catalyst system leading to ring-closing metathesis with the second generation Grubbs' catalyst (10%) followed by dehydrogenation in the presence of RuCl3 × H2O (2%).
Dieltiens, Nicolai,Stevens, Christian V.,Vos, David De,Allaert, Bart,Drozdzak, Renata,Verpoort, Francis
p. 8995 - 8998
(2007/10/03)
Rhodium-Catalysed Reactions of Propargylamines with CO/H2. Formation of Pyrroles and Butenolides
Rhodium-catalysed reactions of (arylpropargyl)amines with CO/H2 give β-arylpyrroles in good yields.Reactions of (alkylpropargyl)amines gave alkylpyrroles together with butenolides which are formed in an unusual reaction that probably involves double carbonylation, reduction of one carbonyl function and removal of the amine function by hydrogenolysis.The single-crystal X-ray structure of 5-methyl-N,3-diphenylpyrrole-2-carboxamide is recorded.
Campi, Eva M.,Fallon, Gary D.,Jackson, W. Roy,Nilsson, Ylva
p. 1167 - 1178
(2007/10/02)
FORMATION OF 1-SUBSTITUTED PYRROLES IN REACTION OF 2-CHLOROCYCLOPROPANECARBOXALDEHYDES WITH PRIMARY AMINES
Reactions of 2-chlorocyclopropanecarboxaldehydes with primary amines in boiling DMF lead in good yield to 1-substituted pyrroles. 2-Chlorocyclopropanecarboxaldehydes were synthesized by the stereoselective reduction of the corresponding 2,2-dichlorocyclopropanemethanols with lithium tetrahydroaluminate with the subsequent oxidation of the mixture of stereoisomeric 2-chlorocyclopropanemethanols with pyridinium chlorochromate.
Nadim, Al' Mokhana,Romashin, Yu. N.,Kulinkovich, O. G.
p. 1419 - 1422
(2007/10/02)
REGIO-AND STEREOSELECTIVE PALLADIUM CATALYZED AMINATION OF ALLYLIC SUBSTRATES. SYNTHESIS OF E-4-AMINO-2-ALKEN-1-OL DERIVATIVES
Under mild conditions 4, 5 and 6 react with primary and secondary amines in the presence of palladium phosphine complexes as catalysts to give 4-amino-2-alken-1-ols with (E) stereochemistry.
Hydroformylation of Bisolefinic Amine Derivatives Catalyzed by Cobalt and Rhodium
Three bisolefinic carbamates and five N,N-diallyl N-substituted amines have been subjected to hydroformylation conditions under catalysis by HCo(CO)4, Co(CO)8 and (Ph3P)3Rh(H)CO in an attempt to prepare heterocyclic ketones.The products differ with amines and carbamates and with catalyst.Carbamate 3 and HCo(CO)4 gave 3-pyrrolidinone (4) in 45percent yield.The cobalt-catalyzed reaction of 8 and rhodium-catalyzed reaction of 3 and of 8 afforded products arising from hydroformylation at the terminal olefinic carbon.These mixtures usually included 2-pyrrolidinone; cobalt-catalyzed hydroformylation of chlorinated allylamines 10-12 provided N-benzyl-2-pyrrolidinone (14) and N,N-dibutylbenzylamine (16).Direct synthesis of potential intermediates including 18 has permitted the delineation of mechanistic rationale.
Garst, Michael E.,Lukton, David
p. 4433 - 4438
(2007/10/02)
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