335605-71-5Relevant academic research and scientific papers
Iron-catalyzed cross-coupling reactions
Fuerstner, Alois,Leitner, Andreas,Mendez, Maria,Krause, Helga
, p. 13856 - 13863 (2002)
Simple iron salts such as FeCln, Fe(acac)n (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl o
Nickel-Catalyzed C(sp2)?C(sp3) Kumada Cross-Coupling of Aryl Tosylates with Alkyl Grignard Reagents
Piontek, Aleksandra,Och?dzan-Siod?ak, Wioletta,Bisz, Elwira,Szostak, Michal
supporting information, p. 2329 - 2336 (2019/04/13)
Aryl tosylates are an attractive class of electrophiles for cross-coupling reactions due to ease of synthesis, low price, and the employment of C?O electrophiles, however, the reactivity of aryl tosylates is low. Herein, we report the Ni-catalyzed C(sp2)?C(sp3) Kumada cross-coupling of aryl tosylates with primary and secondary alkyl Grignard reagents. The method delivers valuable alkyl arenes by cross-coupling with challenging alkyl organometallics possessing β-hydrogens that are prone to β-hydride elimination and homo-coupling. The reaction is catalyzed by an air- and moisture stable-Ni(II) precatalyst. A broad range of electronically-varied aryl tosylates, including bis-tosylates, underwent this transformation, and many examples are suitable at mild room temperature conditions. The combination of Ar?X cross-coupling with the facile Ar?OH activation/cross-coupling strategy permits for orthogonal cross-coupling with challenging alkyl organometallics. Furthermore, we demonstrate that the method operates with TON reaching 2000, which is one of the highest turnovers observed to date in Ni-catalyzed cross-couplings. (Figure presented.).
Iron-catalyzed cross-coupling reactions of alkyl-Grignard reagents with aryl chlorides, tosylates, and triflates
Fuerstner, Alois,Leitner, Andreas
, p. 609 - 612 (2007/10/03)
Aryl chlorides are better substrates than the corresponding bromides or iodides in the presented cross-coupling with alkyl Grignard reagents that is catalyzed by iron salts (see scheme); even aryl tosylates are converted efficiently. This situation is att
General and user-friendly method for Suzuki reactions with aryl chlorides
Fürstner,Leitner
, p. 290 - 292 (2007/10/03)
Through the use of Pd(OAc)2 and the sterically hindered imidazolium salt 5 (IPr·HCl) as the pre-catalyst mixture, aryl chlorides undergo efficient cross coupling reactions with 9-R-9-BBN derivatives (R = alkyl, allyl, alkynyl, cyclopropyl) in the presence of KOMe as the base. This procedure is easily scaleable and applies to electron poor and electron rich substrates with similar ease.
