17024-05-4Relevant articles and documents
Boracene-based alkylborate enabled Ni/Ir hybrid catalysis
Hosoya, Takamitsu,Miyamoto, Yusuke,Ohmiya, Hirohisa,Sato, Yukiya,Sumida, Yuto
supporting information, p. 6598 - 6601 (2020/10/02)
Boracene-based alkylborate enabled visible light-mediated metallaphotoredox catalysis. The directly excited borate was easily oxidatively quenched by an excited Ir photoredox catalyst. Ni/Ir hybrid catalysis afforded the products under significantly low i
Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis
McAtee, Christopher C.,Riehl, Paul S.,Schindler, Corinna S.
supporting information, p. 2960 - 2963 (2017/03/11)
Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.
An N-heterocyclic carbene-based nickel catalyst for the Kumada–Tamao–Corriu coupling of aryl bromides and tertiary alkyl Grignard reagents
Ando, Shin,Mawatari, Mai,Matsunaga, Hirofumi,Ishizuka, Tadao
supporting information, p. 3287 - 3290 (2016/07/11)
In this study, nickel-catalyzed coupling reactions between arylhalides and tert-alkyl Grignard reagents were developed. Our original bicyclic NHC ligands reduced the formation of isomerized products, and we found that NMP as a co-solvent suppressed the reduction process. Under the optimal conditions we developed, the catalyst loading was lowered to 0.5?mol?%, and catalyst loading using ortho-substituted aryl bromides was also applicable at the level of 2.0?mol?%.
Nickel-catalyzed cross-coupling of aryl bromides with tertiary grignard reagents utilizing donor-functionalized N-heterocyclic carbenes (NHCs)
Lohre, Claudia,Droege, Thomas,Wang, Congyang,Glorius, Frank
supporting information; experimental part, p. 6052 - 6055 (2011/06/25)
Metal-catalyzed cross-coupling reactions are among the most important transformations in organic synthesis, allowing the efficient construction of complex structures from simpler, readily available building blocks.Many applications in large and small-scale synthesis can be found in different areas such as agrochemicals, pharmaceuticals and supramolecular chemistry. Whereas the coupling of sp2-hybridized carbon atoms in either reaction partner is well established, the use of CACHTUNGTRENUNG(sp3)-hybridized substrates presents some challenges. Catalytic cross-coupling of sterically hindered tertiary alkyl substrates is especially difficult, generally resulting in low yields, and thus, only few reports exist.[27] A big challenge in this field is not only to get the required level of reactivity, but also to overcome competing pathways like β-hydride elimination, hydrodehalogenation or isomerization
Ene reaction of arynes with alkynes
Jayanth, Thiruvellore Thatai,Jeganmohan, Masilamani,Cheng, Mu-Jeng,Chu, San-Van,Cheng, Chien-Hong
, p. 2232 - 2233 (2007/10/03)
Arynes, generated in situ from ortho-silylaryl triflates, undergo ene reaction with alkynes possessing propargylic hydrogen in the presence of KF/18-crown-6 in THF at room temperature to give substituted phenylallenes. Various terminal and internal alkyne
