2948-44-9Relevant articles and documents
Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents
Chen, Tie-Gen,Zhang, Haolin,Mykhailiuk, Pavel K.,Merchant, Rohan R.,Smith, Courtney A.,Qin, Tian,Baran, Phil S.
, p. 2454 - 2458 (2019/02/09)
This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.
Versatile friedel-crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system
Yamamoto, Yoshihiko,Itonaga, Kouhei
experimental part, p. 10705 - 10715 (2009/12/01)
A variety of molybdenum complexes catalyze Friedel-Crafts-type alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)6] and two equivalents of o-chloranil catalytically furnished the hydroarylation product of norbornene with p-xylene at 80°C, whereas [Cr(CO)6] and [W(CO)6] failed to catalyze the same reaction, thus indicating the importance of the molybdenum source. The best results were obtained when a molybdenum(II) complex [CpMoCl(CO)3] (Cp = cyclopentadienyl) was used as a precatalyst. The hydroarylation reactions also took place with styrenes, cyclohexenes, and 1 -hexene as olefin substrates. The electrophilic-substitution mechanism was proposed on the basis of the ortho/para selectivities and the Markovnikov selectivities observed for the hydroarylation products. Our hypothesis was further corroborated by the fact that in the presence of the [CpMoCl(CO)3]/o-chloranil catalytic system, secondary, benzylic, or allylic alcohols participated in the alkylation of benzenes with similar selectivities.
Gallium Dichloride-Mediated Reductive Friedel-Crafts Reaction
Hashimoto, Yukihiko,Hirata, Kazujuki,Kagoshima, Hirotaka,Kihara, Nobuhiro,Hasegawa, Masaki,Saigo, Kazuhiko
, p. 5969 - 5978 (2007/10/02)
In the presence of gallium dichloride, the reaction of carbonyl compounds or their dimethylacetals with aromatic compounds afforded Friedel-Crafts alkylated adducts in good yields.It was suggested that the adducts were obtained by way of a reduction of the carbonyl compounds or their dimethylacetals, followed by the Friedel-Crafts reaction in one-pot.This is the first organic synthetic method with gallium dichloride, low valent gallium.
