70810-18-3Relevant articles and documents
A surprising substituent effect provides a superior boronic acid catalyst for mild and metal-free direct Friedel-Crafts alkylations and prenylations of neutral arenes
Ricardo, Carolynne L.,Mo, Xiaobin,McCubbin, J. Adam,Hall, Dennis G.
supporting information, p. 4218 - 4223 (2015/03/14)
The development of more general and efficient catalytic processes for Friedel-Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5-tetrafluorophenylboronic acid was identified as a potent air- and moisture-tolerant metal-free catalyst that significantly improves the scope of direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.
Allylic activation across an Ir-Sn heterobimetallic catalyst: Nucleophilic substitution and disproportionation of allylic alcohol
Chatterjee, Paresh Nath,Roy, Sujit
supporting information; experimental part, p. 3776 - 3785 (2012/07/14)
A nucleophilic substitution of allylic alcohols with carbon (arene, heteroarene, allyltrimethylsilane, and 1,3-dicarbonyl compound), sulfur (thiol), oxygen (alcohol), and nitrogen (sulfonamide) nucleophiles has been demonstrated using an in house developed [Ir(COD)(SnCl3)l(μ-Cl)]2 heterobimetallic catalyst in 1,2-dichloroethane to afford the corresponding allylic products in moderate to excellent yields. In 4-hydroxycoumarin, allylation occurs at the 3-position. The diaryl-substituted allylic alcohols undergo disproportionation in presence of the heterobimetallic catalyst to provide the corresponding alkenes and chalcones. An electrophilic mechanism is proposed from Hammett correlation study.
Homogeneous silver(I) salts and heterogeneous Ag3PW 12O40-catalyzed intermolecular allylation of arenes with allylic alcohols
Chen, Guo-Qiang,Xu, Zhen-Jiang,Chan, Sharon Lai-Fung,Zhou, Cong-Ying,Che, Chi-Ming
supporting information; experimental part, p. 2713 - 2718 (2011/12/04)
AgOTf is an effective catalyst for intermolecular allylation of aromatic and heteroaromatic compounds with allylic alcohols affording allylated arenes in up to 99% yields. Heterogeneous allylation of arenes catalyzed by Ag 3PW12O40 gave comparable product yields to those obtained by AgOTf. Ag3PW12O40 could be reused five times with slightly decreased activity. Georg Thieme Verlag Stuttgart · New York.
A convenient and improved montmorillonite K-10 catalysed Friedel-Crafts benzylation and allylation with activated esters
Karade,Shirodkar,Potrekar
, p. 652 - 654 (2007/10/03)
Benzyl benzoate and cinnamyl acetate has been effectively used respectively as alkylating and allylating substrates in Friedel-Crafts reaction catalysed by montmorillonite K-10 clay.
Coupling Reaction of Allylstannanes with Arenes
Yamaguchi, Jun-ichi,Takagi, Yu,Nakayama, Atsushi,Fujiwara, Tooru,Takeda, Takeshi
, p. 133 - 136 (2007/10/02)
The tin(IV) chloride promoted coupling reaction of allylstannanes with various arenes proceeded to give the allylated arenes in good yields.It was also found that tin(II) bromide was an effective catalyst for Friedel-Crafts allylation using allylic bromid