136608-30-5Relevant articles and documents
Room-temperature Hiyama cross-couplings of arylsilanes with alkyl bromides and iodides
Lee, Jae-Young,Fu, Gregory C.
, p. 5616 - 5617 (2003)
The first method for achieving Hiyama couplings of unactivated alkyl bromides and iodides is reported. The desired carbon-carbon bond formation proceeds under mild conditions (room temperature) with good functional-group tolerance. Copyright
Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism
Zhang, Wen,Lin, Song
supporting information, p. 20661 - 20670 (2020/12/23)
Electrochemistry grants direct access to reactive intermediates (radicals and ions) in a controlled fashion toward selective organic transformations. This feature has been demonstrated in a variety of alkene functionalization reactions, most of which proceed via an anodic oxidation pathway. In this report, we further expand the scope of electrochemistry to the reductive functionalization of alkenes. In particular, the strategic choice of reagents and reaction conditions enabled a radical-polar crossover pathway wherein two distinct electrophiles can be added across an alkene in a highly chemo- and regioselective fashion. Specifically, we used this strategy in the intermolecular carboformylation, anti-Markovnikov hydroalkylation, and carbocarboxylation of alkenes - reactions with rare precedents in the literature - by means of the electroreductive generation of alkyl radical and carbanion intermediates. These reactions employ readily available starting materials (alkyl halides, alkenes, etc.) and simple, transition-metal-free conditions and display broad substrate scope and good tolerance of functional groups. A uniform protocol can be used to achieve all three transformations by simply altering the reaction medium. This development provides a new avenue for constructing Csp3-Csp3 bonds.
