51755-56-7Relevant articles and documents
para-Selective Benzylation of Aryl Iodides by the in situ Preparation of ArIF2: a Hypervalent Iodine-Guided Electrophilic Substitution
Chaudhry, Azka,Hyatt, I. F. Dempsey,Im, Haram,Jones, Taro J.,Noorollah, Jennifer,Siddiqi, Fatima,Singh, Nirvanie,Spatola, Nicholas R.
supporting information, (2020/04/16)
Hypervalent iodine-guided electrophilic substitution (HIGES) was described previously for the para-selective benzylation of aryl-λ3-iodane diacetates. One drawback of the method was the synthesis and isolation of hypervalent iodine starting mat
Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes
Sinha, Narayan,Heijnen, Dorus,Feringa, Ben L.,Organ, Michael G.
supporting information, p. 9180 - 9184 (2019/07/04)
The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.
Palladium-catalyzed C(sp 3)-C(sp 2) cross-coupling of (trimethylsilyl)methyllithium with (hetero)aryl halides
Heijnen, Dorus,Hornillos, Valentín,Corbet, Brian P.,Giannerini, Massimo,Feringa, Ben L.
supporting information, p. 2262 - 2265 (2015/05/13)
The palladium-catalyzed direct cross-coupling of a range of organic chlorides and bromides with the bifunctional C(sp3)-(trimethylsilyl)methyllithium reagent is reported. The use of Pd-PEPPSI-IPent as the catalyst allows for the preparation of structurally diverse and synthetically versatile benzyl- and allylsilanes in high yields under mild conditions (room temperature) with short reaction times.