3840-17-3Relevant articles and documents
Catalytic amide base system generatedin situfor 1,3-diene formation from allylbenzenes and carbonyls
Shigeno, Masanori,Kajima, Akihisa,Nakaji, Kunihito,Nozawa-Kumada, Kanako,Kondo, Yoshinori
supporting information, p. 983 - 987 (2021/02/16)
The amide base generatedin situfrom tetramethylammonium fluoride and N(TMS)3catalyzes the synthesis of 1,3-diene from an allylbenzene and carbonyl compound. The system is applicable to the transformations of a variety of allylbenzenes with functional groups (halogen, methyl, phenyl, methoxy, dimethylamino, ester, and amide moieties). Acyclic and cyclic diaryl ketones, pivalophenone, pivalaldehyde, and isobutyrophenone are used as coupling partners. The role oftransβ-methyl stilbenes in product formation is also elucidated.
Cross-Coupling Reactions of Aryldiazonium Salts with Allylsilanes under Merged Gold/Visible-Light Photoredox Catalysis
Akram, Manjur O.,Mali, Pramod S.,Patil, Nitin T.
supporting information, p. 3075 - 3078 (2017/06/23)
A method for the cross-coupling reactions of aryldiazonium salts with trialkylallylsilanes via merged gold/photoredox catalysis is described. The reaction is proposed to proceed through a photoredox-promoted generation of an electrophilic arylgold(III) intermediate that undergoes transmetalation with allyltrimethylsilane to form allylarenes.
Anti-Markovnikov rearrangement in sulfur mediated allylic C-H amination of olefins
Zhang, Zhong,Du, Hongguang,Xu, Jiaxi,Li, Pingfan
supporting information, p. 11547 - 11550 (2016/10/03)
Cationic rearrangement reactions usually follow Markovnikov's rule to give more substituted carbocations as stable intermediates. During our study on sulfur mediated allylic C-H amination of olefins, very rare cases of anti-Markovnikov rearrangement from secondary carbocations toward primary carbocations or primary triflates were observed.
Nickel-catalyzed heck-type reactions of benzyl chlorides and simple olefins
Matsubara, Ryosuke,Gutierrez, Alicia C.,Jamison, Timothy F.
supporting information; experimental part, p. 19020 - 19023 (2011/12/21)
Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity.
Remarkable regioselectivity in microwave-enhanced palladium-catalyzed allylation reaction involving allyltrifluoroborates and aryl halides
Al-Masum, Mohammad,Alam, Shahrina
scheme or table, p. 5201 - 5204 (2009/12/06)
An unprecedented cross-coupling reaction of potassium allyltrifluoroborates and aryl halides to the corresponding trans-β-methylstyrenes in the presence of PdCl2(dtbpf) catalyst under microwave heating was developed.
Process of heterocoupling by electrolytic microbattery, use of cobalt for implementing said coupling and composition for doing so
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Page 12-13, (2008/06/13)
This invention has as its object a process for preparation of vinyl aryl derivatives by an electrochemical path. This process is defined in that it consists in subjecting a composition that comprises a cobalt salt, an aromatic halide and a vinyl ester to the action of a metal that is at least as reducing as zinc. Application to organic synthesis.
Design, synthesis and cytotoxicity of 7-deoxy aryl discodermolide analogues
Burlingame, Mark A.,Shaw, Simon J.,Sundermann, Kurt F.,Zhang, Dan,Petryka, Joseph,Mendoza, Esteban,Liu, Fenghua,Myles, David C.,LaMarche, Matthew J.,Hirose, Tomoyasu,Freeze, B. Scott,Smith III, Amos B.
, p. 2335 - 2338 (2007/10/03)
A series of 7-deoxy discodermolide analogues in which the lactone fragment 'C' was replaced by aryl substituents were designed, synthesized, and evaluated for cytotoxicity.
Cobalt-catalyzed direct electrochemical cross-coupling between aryl or heteroaryl halides and allylic acetates or carbonates
Gomes, Paulo,Gosmini, Corinne,Perichon, Jacques
, p. 1142 - 1145 (2007/10/03)
The electroreduction of a mixture of functionalized aromatic or heteroaromatic bromides or chlorides and allylic compounds such as acetates or carbonates in an electrochemical cell fitted with a sacrificial iron anode affords, in the presence of cobalt halide associated with pyridine as ligand in acetonitrile or DMF, the corresponding coupling product in good yields.
New chemical cross-coupling between aryl halides and allylic acetates using a cobalt catalyst
Gomes, Paulo,Gosmini, Corinne,Perichon, Jacques
, p. 1043 - 1045 (2007/10/03)
(Figure presented) The cobalt-catalyzed coupling reaction of aromatic halides and allylic acetates proceeds readily under mild conditions in the presence of the appropriate reducing agent to produce allylaromatic derivatives either in pure acetonitrile (aryl bromides) or in an acetonitrile/pyridine mixture (aryl chlorides).
Protonation and Alkykation of 1-Arylpropenyl-lithium
Tanaka, Jiro,Nojima, Masatomo,Kusabayashi, Shigekazu,Nagase, Shigeru
, p. 673 - 678 (2007/10/02)
The protonation and alkylation of 1-arylpropenyl-lithium (1a-c) in ether was undertaken systematically; the regio- and stereo-chemistry being influenced by various factors.The characteristic features are as follows. (a) Protonation occurs predominantly at C-3, whereas the sterically more crowded C-1 is the more favoured site for alkylation, and (b) although 1-arylpropenyl-lithium (1) seems to exist mainly as the E-isomer, in some cases the product (3) or (5) having the Z-configuration is produced from attack at C-3 in a significant amount together with the E-isomer, e.g. protonation by oxygen acids in the presence or absence of tetramethylethylenediamine and methylation of the p-methoxy derivative (1a).
