406233-04-3Relevant articles and documents
Silyl Radical Activation of Alkyl Halides in Metallaphotoredox Catalysis: A Unique Pathway for Cross-Electrophile Coupling
Zhang, Patricia,Le, Chi Chip,MacMillan, David W. C.
, p. 8084 - 8087 (2016)
A strategy for cross-electrophile coupling has been developed via the merger of photoredox and transition metal catalysis. In this report, we demonstrate the use of commercially available tris(trimethylsilyl)silane with metallaphotoredox catalysis to efficiently couple alkyl bromides with aryl or heteroaryl bromides in excellent yields. We hypothesize that a photocatalytically generated silyl radical species can perform halogen-atom abstraction to activate alkyl halides as nucleophilic cross-coupling partners. This protocol allows the use of mild yet robust conditions to construct Csp3-Csp2 bonds generically via a unique cross-coupling pathway.
Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: Sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides
Zhang, Xiaheng,MacMillan, David W.C.
supporting information, p. 13862 - 13865 (2016/11/06)
Alkyl oxalates, prepared from their corresponding alcohols, are engaged for the first time as carbon radical fragments in metallaphotoredox catalysis. In this report, we demonstrate that alcohols, native organic functional groups, can be readily activated with simple oxalyl chloride to become radical precursors in a net redox-neutral Csp3-Csp2 cross-coupling with a broad range of aryl halides. This alcohol-activation coupling is successfully applied to the functionalization of a naturally occurring steroid and the expedient synthesis of a medicinally relevant drug lead.
Iron-catalyzed Suzuki-Miyaura coupling of alkyl halides
Hatakeyama, Takuji,Hashimoto, Toru,Kondo, Yoshiyuki,Fujiwara, Yuichi,Seike, Hirofumi,Takaya, Hikaru,Tamada, Yoshinori,Ono, Teruo,Nakamura, Masaharu
supporting information; experimental part, p. 10674 - 10676 (2010/11/04)
In the presence of novel iron(II) chloride-diphosphine complexes and magnesium bromide, lithium arylborates react with primary and secondary alkyl halides to give the corresponding coupling products in good to excellent yields. High functional group compa