251928-75-3Relevant articles and documents
Electrochemical Hydroboration of Alkynes
Aelterman, Maude,Jubault, Philippe,Poisson, Thomas,Sayes, Morgane
supporting information, p. 8277 - 8282 (2021/05/27)
Herein we reported the electrochemical hydroboration of alkynes by using B2Pin2 as the boron source. This unprecedented reaction manifold was applied to a broad range of alkynes, giving the hydroboration products in good to excellent yields without the need of a metal catalyst or a hydride source. This transformation relied on the possible electrochemical oxidation of an in situ formed borate. This anodic oxidation performed in an undivided cell allowed the formation of a putative boryl radical, which reacted on the alkyne.
Cobalt-Catalyzed Markovnikov-Type Selective Hydroboration of Terminal Alkynes
Chen, Jieping,Shen, Xuzhong,Lu, Zhan
supporting information, p. 690 - 694 (2020/11/30)
A cobalt-catalyzed Markovnikov-type hydroboration of terminal alkynes with HBpin to access α-alkenyl boronates with good regioselectivity and atom economy is reported. A new ligand has been developed for the cobalt hydride catalyst that has been used for a unique Markovnikov selective insertion of terminal alkynes into metal hydride bond. This operationally simple protocol exhibits excellent functional group tolerance to deliver valuable alkene derivatives.
Copper-Catalyzed Triboration: Straightforward, Atom-Economical Synthesis of 1,1,1-Triborylalkanes from Terminal Alkynes and HBpin
Liu, Xiaocui,Ming, Wenbo,Zhang, Yixiao,Friedrich, Alexandra,Marder, Todd B.
, p. 18923 - 18927 (2019/11/22)
A convenient and efficient one-step synthesis of 1,1,1-triborylalkanes was achieved via sequential dehydrogenative borylation and double hydroborations of terminal alkynes with HBpin (HBpin=pinacolborane) catalyzed by inexpensive and readily available Cu(OAc)2. This process proceeds under mild conditions, furnishing 1,1,1-tris(boronates) with wide substrate scope, excellent selectivity, and good functional-group tolerance, and is applicable to gram-scale synthesis without loss of yield. The 1,1,1-triborylalkanes can be used in the preparation of α-vinylboronates and borylated cyclic compounds, which are valuable but previously rare compounds. Different alkyl groups can be introduced stepwise via base-mediated deborylative alkylation to produce racemic tertiary alkyl boronates, which can be readily transformed into useful tertiary alcohols.
