460088-33-9Relevant articles and documents
Cobalt-Catalyzed C(sp2)-C(sp3) Suzuki-Miyaura Cross Coupling
Ludwig, Jacob R.,Simmons, Eric M.,Wisniewski, Steven R.,Chirik, Paul J.
supporting information, (2020/11/02)
A cobalt-catalyzed method for the C(sp2)-C(sp3) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides is described. Cobalt-ligand combinations were assayed with high-throughput experimentation, and cobalt(II) sources with trans-N,N′-dimethylcyclohexane-1,2-diamine (DMCyDA, L1) produced optimal yield and selectivity. The scope of this transformation encompassed steric and electronic diversity on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile. Radical trap experiments support the formation of electrophile-derived radicals during catalysis.
Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: Control of absolute stereochemistry with an achiral catalyst
Harris, Michael R.,Hanna, Luke E.,Greene, Margaret A.,Moore, Curtis E.,Jarvo, Elizabeth R.
supporting information, p. 3303 - 3306 (2013/04/10)
Stereospecific coupling of benzylic carbamates and pivalates with aryl- and heteroarylboronic esters has been developed. The reaction proceeds with selective inversion or retention at the electrophilic carbon, depending on the nature of the ligand. Tricyclohexylphosphine ligand provides the product with retention, while an N-heterocyclic carbene ligand provides the product with inversion.
Borylation of organo halides and triflates using tetrakis(dimethylamino) diboron
Bello, Charles S.,Schmidt-Leithoff, Joachim
, p. 6230 - 6235,6 (2012/12/11)
We report a new in situ borylation method using tetrakis(dimethylamino) diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic ester for subsequent Suzuki coupling.