1009-33-2Relevant academic research and scientific papers
Silylium-Ion-Promoted (5+1) Cycloaddition of Aryl-Substituted Vinylcyclopropanes and Hydrosilanes Involving Aryl Migration
Bonetti, Vittorio,He, Tao,Klare, Hendrik F. T.,Oestreich, Martin,Wang, Guoqiang
supporting information, p. 12186 - 12191 (2020/05/22)
A transition-metal-free (5+1) cycloaddition of aryl-substituted vinylcyclopropanes (VCPs) and hydrosilanes to afford silacyclohexanes is reported. Catalytic amounts of the trityl cation initiate the reaction by hydride abstraction from the hydrosilane, and further progress of the reaction is maintained by self-regeneration of the silylium ions. The new reaction involves a [1,2] migration of an aryl group, eventually furnishing 4- rather than 3-aryl-substituted silacyclohexane derivatives as major products. Various control experiments and quantum-chemical calculations support a mechanistic picture where a silylium ion intramolecularly stabilized by a cyclopropane ring can either undergo a kinetically favored concerted [1,2] aryl migration/ring expansion or engage in a cyclopropane-to-cyclopropane rearrangement.
Difluoroalkylation/C-H Annulation Cascade Reaction Induced by Visible-Light Photoredox Catalysis
Li, Jin,Chen, Jingzhi,Jiao, Wei,Wang, Guoqiang,Li, Ying,Cheng, Xu,Li, Guigen
, p. 9992 - 10001 (2016/10/31)
We report the first example of difluoroalkylation/C-H annulation cascade reactions of cyclopropyl olefins induced by visible-light photoredox catalysis regioselectively affording partially hydrogenated naphthalenes and quinolines with a variety of difluorinated side chains. The alkylation reagent could be extended to monofluoro and trifluoro reagents, nitrile and malonate. The regioselectivity was investigated by means of density functional theory calculations.
Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
Vila, Carlos,Giannerini, Massimo,Hornillos, Valentin,Fananas-Mastral, Martin,Feringa, Ben L.
, p. 1361 - 1367 (2014/03/21)
Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C-C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.
Pinacolboratamethyl-enetriphenylphosphonium iodide, a new methylene transfer reagent
Al-Aziz Quntar, Abed,Srebnik, Morris
, p. 2575 - 2579 (2007/10/03)
The title compound is easily prepared and reacts with various aldehydes and ketone. The reagent is compatible with free hydroxy groups. Yields with various aldehydes and ketones are in 50- > 99% range. Both aliphatic, aromatic and unsaturated carbonyls react.
Insecticidal cyclopropyl-substituted di(aryl) compounds
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, (2008/06/13)
Compounds of the formula STR1 in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
REACTION OF 2,2-DISUBSTITUTED 1-(DIBROMOMETHYLENE)CYCLOPROPANES WITH METHYLLITHIUM
Kostikov, R. R.,Molchanov, A. P.,Nagi, Sh. M.
, p. 1291 - 1297 (2007/10/02)
In the reaction of 2,2-disubstituted 1-(dibromomethylene)cyclopropanes with methyllithium 4,4-disubstituted 1-buten-3-ynes and 2,2-disubstituted (1-bromoethylidene)cyclopropanes are formed in ratios which depend on the character of substitution in the cyclopropane ring.
