1612155-99-3Relevant articles and documents
Ru/Ni Dual Catalytic Desulfinative Photoredox Csp2-C sp3Cross-Coupling of Alkyl Sulfinate Salts and Aryl Halides
Knauber, Thomas,Chandrasekaran, Ramalakshmi,Tucker, Joseph W.,Chen, Jinshan Michael,Reese, Matthew,Rankic, Danica A.,Sach, Neal,Helal, Christopher
, p. 6566 - 6569 (2017)
A mild Ru/Ni dual catalytic desulfinative photoredox Csp2-Csp3 cross-coupling reaction of alkyl sulfinate salts with aryl halides has been developed. The optimized catalyst system, consisting of Ru(bpy)3Cl2, Ni(COD)2, and DBU, smoothly mediates the coupling of a diverse set of secondary and primary nonactivated alkyl sulfinate salts with a broad range of electron-deficient aryl bromides, electron-rich aryl iodides, and heteroaryl bromides under irradiation with blue light. The procedure is ideal for late-stage introduction of alkyl groups on pharmaceutical intermediates, and the Csp2-Csp3 cross-coupling reaction allowed the rapid synthesis of caseine kinase 1 inhibitor analogues via a parallel medicinal chemistry effort.
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.
supporting information, p. 8084 - 8087 (2016/07/16)
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.
