20498-68-4Relevant articles and documents
Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides
Potrz?saj, Aleksandra,Musiejuk, Mateusz,Cha?adaj, Wojciech,Giedyk, Maciej,Gryko, Dorota
supporting information, p. 9368 - 9376 (2021/06/28)
Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report that the vitamin B12/Ni dual-catalytic system allows for the selective synthesis of linear products under blue-light irradiation, thus complementing methodologies that give access to branched alcohols. Experimental and theoretical studies corroborate the proposed mechanism involving alkylcobalamin as an intermediate in this reaction.
Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles
Thapa, Surendra,Dhungana, Roshan K.,Magar, Rajani Thapa,Shrestha, Bijay,Kc, Shekhar,Giri, Ramesh
, p. 904 - 909 (2018/02/07)
We report a Ni-catalysed diarylation of unactivated olefins in dimethylpyridylvinylsilane by intercepting Heck C(sp3)-NiX intermediates, derived from aryl halides, with arylzinc reagents. This approach utilizes a modifiable pyridylsilyl moiety as a coordinating group that plays a dual role of intercepting oxidative addition species to promote Heck carbometallation, and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination, and facilitate transmetalation/reductive elimination. This method affords 1,2-diarylethylsilanes, which can be readily oxidized to 1,2-diarylethanols that occur as structural motifs in 3-aryl-3,4-dihydroisocoumarin and dihydrostilbenoid natural products.
Catalytic functionalization of methyl group on silicon: Iridium-catalyzed C(sp3)-H borylation of methylchlorosilanes
Ohmura, Toshimichi,Torigoe, Takeru,Suginome, Michinori
supporting information, p. 17416 - 17419,4 (2012/12/12)
A methyl group of methylchlorosilanes undergoes C-H borylation in an iridium-catalyzed reaction with bis(pinacolato)diboron in cyclohexane at 80 °C, giving (borylmethyl)chlorosilanes selectively.