838821-67-3Relevant academic research and scientific papers
Cobalt-mediated diastereoselective cross-coupling reactions between cyclic halohydrins and arylmagnesium reagents
Hammann, Jeffrey M.,Steib, Andreas K.,Knochel, Paul
, p. 6500 - 6503 (2014)
Cyclic TBS-protected iodohydrins (and bromohydrins) undergo a highly diastereoselective cross-coupling with various aryl- and heteroarylmagnesium reagents in the presence of THF-soluble CoCl2·2LiCl and TMEDA as a ligand leading to trans-2-arylcyclohexanol derivatives in good yields and dr up to >99:1. A range of functional groups are tolerated in the Grignard reagent (e.g., COOR, CN, CF3, SF5). The use of heterocyclic iodohydrins leads to trans-3,4-disubstituted pyrrolidines and tetrahydrofurans.
Amino alcohols as ligands for nickel-catalyzed Suzuki reactions of unactivated alkyl halides, including secondary alkyl chlorides, with arylboronic acids
Gonzalez-Bobes, Francisco,Fu, Gregory C.
, p. 5360 - 5361 (2007/10/03)
Suzuki cross-coupling reactions of an unprecedented array of unactivated primary and secondary alkyl halides (including challenging alkyl chlorides) can be accomplished through the use of nickel/amino alcohol-based catalysts. Both the nickel precatalyst and the amino alcohols (prolinol or trans-2-aminocyclohexanol) are commercially available and air-stable. In view of the remarkable diversity of amino alcohols that are readily accessible, this discovery may open the door to the rapid development of versatile catalysts for a wide range of cross-coupling processes. Copyright
Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents
Powell, David A.,Maki, Toshihide,Fu, Gregory C.
, p. 510 - 511 (2007/10/03)
The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2′-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products. Copyright
