1025-23-6Relevant articles and documents
Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex
Xie, Jin,Li, Jian,Weingand, Vanessa,Rudolph, Matthias,Hashmi, A. Stephen K.
, p. 12646 - 12650 (2016)
A practical protocol for a photocatalyzed alkyl-Heck-like reaction of unactivated alkyl bromides and different alkenes promoted by dinuclear gold photoredox catalysis in the presence of an inorganic base is reported. Primary, secondary, and tertiary unactivated alkyl bromides with β-hydrogen can be applied. Esters, aldehydes, ketones, nitriles, alcohols, heterocycles, alkynes, alkenes, ethers, and halogen moieties are all well tolerated. In addition to 1,1-diarylalkenes, silylenolethers and enamides can also be applied, which further increases the synthetic potential of the reaction. The mild reaction conditions, broad substrate scope, and an excellent functional-group tolerance deliver an ideal tool for synthetic chemists that can even be used for challenging late-stage modifications of complex natural products.
Nickel-catalyzed ring-opening cross-coupling of cyclic alkenyl ethers with arylboronic esters via carbon-oxygen bond cleavage
Ohtsuki, Akimichi,Sakurai, Shun,Tobisu, Mamoru,Chatani, Naoto
supporting information, p. 1277 - 1279 (2016/11/09)
We have developed a nickel-catalyzed cross-coupling reaction of cyclic alkenyl ethers with arylboronic esters that leads to the formation of unsaturated alcohols via ring-opening by the cleavage of a C(sp2)-O bond. The use of 1,3-dicyclohexylimidazol-2-ylidene as the ligand is essential to promote this cross-coupling process.
Intramolecular polar addition reactions of active methylene moieties to aryl-substituted alkenes via photoinduced electron transfer
Ohashi, Maki,Nakatani, Keisuke,Maeda, Hajime,Mizuno, Kazuhiko
scheme or table, p. 5537 - 5539 (2010/11/03)
The synthesis of cycloalkane derivatives with ring sizes of 5-7 was achieved in moderate yields by photoirradiation of aqueous acetonitrile solutions, containing compounds that consist of active methylene moieties tethered to aryl-substituted alkenes along with sodium hydroxide and 9-cyanophenanthrene. When the substrate contains ethyl cyanoacetate as an asymmetric active methylene moiety, the reaction proceeds in a highly diastereoselective manner.