35357-77-8Relevant articles and documents
Ruthenium catalysts for controlled mono- and bis-allylation of active methylene compounds with aliphatic allylic substrates
Zhang, Hui-Jun,Demerseman, Bernard,Xi, Zhenfeng,Bruneau, Christian
, p. 2724 - 2728 (2009)
The allylation of 1,3-dicarbonyl compounds and malononitrile with aliphatic allylic substrates is achieved under mild conditions in the presence of new ruthenium catalysts. The ruthenium complex [Ru(C5Me5) (2-quinolinecarboxylato)(CH
Sulfur-mediated radical cyclisation reactions on solid support
Harrowven, David C.,May, Peter J.,Bradley, Mark
, p. 503 - 506 (2003)
Two methods for effecting radical cyclisation reactions of solid-supported 1,6-dienes are described. Additions of thiophenol and p-tolyl benzeneselenosulfonate have each been achieved with a concomitant 5-exo-trig radical cyclisation leading to the formation of highly functionalised cyclopentanes.
Allylic alkylation and ring-closing metathesis in sequence: A successful cohabitation of Pd and Ru
Kammerer, Claire,Prestat, Guillaume,Gaillard, Thomas,Madec, David,Poli, Giovanni
, p. 405 - 408 (2008)
An allylic alkylation/ring-closing metathesis domino catalytic process, wherein a palladium and a ruthenium catalyst are concomitantly present in the reaction mixture from the outset of the reaction, is developed. Evidence for Grubbs' catalysts activity in allylic alkylation is also reported.
FIVE VS SIX MEMBERED RING FORMATION IN THE VINYL RADICAL CYCLIZATION
Stork, Gilbert,Mook, Robert
, p. 4529 - 4532 (1986)
The ratio of methylenecyclopentane to methylenecyclohexane derivatives observed in the vinyl radical cyclization increases with the concentration of substrate and tin hydride.This is interpreted to mean that these cyclizations are under thermodynamic control at low concentrations.
2,4,6-Triphenylpyridine as a Neutral Leaving Group in the Palladium(0)-Catalyzed Allylation of Nucleophiles
Moreno-Manas,Morral,Pleixats
, p. 241 - 246 (1997)
Palladium(0)-catalyzed allylation of nucleophiles such as morpholine, sodium dimethyl malonate and 2,6-dimethylaniline can be achieved under very mild conditions using N-allyl-2,4,6-triphenylpyridinium tetrafluoroborates as allylating reagents in reactions in which 2,4,6-triphenylpyridine acts as the neutral leaving group.
ALLYATION OF CARBONUCLEOPHILES WITH ALLYLIC CARBONATES UNDER NEUTRAL CONDITIONS CATALYZED BY RHODIUM COMPLEXES
Tsuji, Jiro,Minami, Ichiro,Shimizu, Isao
, p. 5157 - 5160 (1984)
Rhodium-phosphine complexes catalyze the allylation of carbonucleophiles with allylic carbonates under neutral conditions.In addition, we found unusual regioselectivity in the rhodium catalyzed allylation.
Methyl Radical Initiated Kharasch and Related Reactions
Tappin, Nicholas D. C.,Renaud, Philippe
supporting information, p. 275 - 282 (2020/12/07)
An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
Catalytic C?C Bond Formation Using a Simple Nickel Precatalyst System: Base- and Activator-Free Direct C-Allylation by Alcohols and Amines
Sweeney, Joseph B.,Ball, Anthony K.,Smith, Luke J.
supporting information, p. 7354 - 7357 (2018/05/03)
A “totally catalytic” nickel(0)-mediated method for base-free direct alkylation of allyl alcohols and allyl amines is reported. The reaction is selective for monoallylation, uses an inexpensive NiII precatalyst system, and requires no activating reagents to be present.
Development of a One-Pot Four C-C Bond-Forming Sequence Based on Palladium/Ruthenium Tandem Catalysis
Manick, Anne-Doriane,Berhal, Farouk,Prestat, Guillaume
supporting information, p. 194 - 197 (2018/01/17)
A one-pot four C-C bond-forming sequence has been developed using two distinct transition metal complexes. The sequence entails a double Pd-catalyzed allylic alkylation followed by a Ru-catalyzed ring-closing metathesis and a Pd-catalyzed Heck coupling. The use of various active methylene nucleophiles was examined with yields up to 76% (93% per C-C bond).
Highly efficient Tsuji-Trost allylation in water catalyzed by Pd-nanoparticles
Llevot,Monney,Sehlinger,Behrens,Meier
supporting information, p. 5175 - 5178 (2017/07/12)
Palladium nanoparticles stabilized by poly(vinylpyrrolidone) catalyze Tsuji-Trost allylations in water with very high turnover numbers. The di-allylation of methylene active compounds and the allylation of bio-based phenols was performed in high yield. The allylation of lignin showed a high selectivity towards the phenolic OH groups.
