144809-36-9Relevant academic research and scientific papers
Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu, Shiwen,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
, p. 3667 - 3671 (2018/09/12)
Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).
Copper-catalyzed hydroalkylation of terminal alkynes
Uehling, Mycah R.,Suess, Alison M.,Lalic, Gojko
supporting information, p. 1424 - 1427 (2015/02/19)
We have developed a copper-catalyzed hydroalkylation of terminal alkynes using alkyl triflates as coupling partners and (Me2HSi)2O as a hydride donor. The hydroalkylation proceeds with excellent anti-Markovnikov regioselectivity and provides exclusively (E)-alkenes. We have demonstrated that both alkyl- and aryl-substituted alkynes can be used as substrates, together with 1° alkyl and benzylic triflates. Finally, the transformation can be accomplished in the presence of a wide range of functional groups. Overall, the new hydroalkylation reaction allows highly efficient and diastereospecific synthesis of (E)-alkenes from readily available terminal alkynes and alkyl triflates. On the basis of a preliminary mechanistic study, we propose that the hydroalkylation reaction involves copper hydride formation, hydrocupration of an alkyne, and alkylation of an alkenyl copper intermediate.
Copper-catalyzed allylic alkylations of alkylzirconium intermediates
Venanzi, Luigi M.,Lehmann, Roman,Keil, Robert,Lipshutz, Bruce H.
, p. 5857 - 5860 (2007/10/02)
Hydrozirconation of olefins followed by exposure of the resulting alkylzirconium species to catalytic CuCN in the presence of activated halides or phosphonates gives rise to products of aklkylation in good yields under mild conditions.
