57981-22-3Relevant academic research and scientific papers
Formal Bromine Atom Transfer Radical Addition of Nonactivated Bromoalkanes Using Photoredox Gold Catalysis
Zidan, Montserrat,McCallum, Terry,Swann, Rowan,Barriault, Louis
supporting information, p. 8401 - 8406 (2020/11/03)
Organic transformations mediated by photoredox catalysis have been at the forefront of reaction discovery. Recently, it has been demonstrated that binuclear Au(I) bisphosphine complexes, such as [Au2(μ-dppm)2]X2, are capable of mediating electron transfer to nonactivated bromoalkanes for the generation of a variety of alkyl radicals. The transfer reactions of bromine, derived from nonactivated bromoalkanes, are largely unknown. Therefore, we propose that unique metal-based mechanistic pathways are at play, as this binuclear gold catalyst has been known to produce Au(III) Lewis acid intermediates. The scope and proposed mechanistic overview for the formal bromine atom transfer reaction of nonactivated bromoalkanes mediated by photoredox Au(I) catalysis is presented. The methodology presented afforded good yields and a broad scope which include examples using bromoalkanes and iodoarenes.
Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis
Venning, Alexander R. O.,Kwiatkowski, Megan R.,Roque Pe?a, Joan E.,Lainhart, Brendan C.,Guruparan, Akil A.,Alexanian, Erik J.
, p. 11595 - 11600 (2017/08/30)
The development of a general catalytic system for the palladium-catalyzed carbocyclization of unactivated alkyl bromides with alkenes is described. This approach uses a commercially available bisphosphine ligand and avoids the use of carbon monoxide atmosphere present in prior studies involving alkyl iodides. Detailed mechanistic studies of the transformation are performed, which are consistent with auto-tandem catalysis involving atom-transfer radical cyclization followed by catalytic dehydrohalogenation. These studies also suggest that reactions involving alkyl iodides may proceed through a metal-initiated, rather than metal-catalyzed, radical chain process.
Reductive alkylation of β-alkoxy aziridines: New route to substituted allylic amines
Rosser, Clare M.,Coole, Susannah C.,Kirby, Jonathan P.,O'Brien, Peter,Caine, Darren
, p. 4817 - 4819 (2007/10/03)
(Chemical Equation Presented) A new route to substituted cyclic allylic amines via the reductive alkylation of β-alkoxy aziridines using excess alkyllithium reagents is described.
