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Regioselective Propargylic Suzuki-Miyaura Coupling by SciPROP-Iron Catalyst
Siming Lu1,2, Ryosuke Agata1,2, Satsuki Nomura1,2
1International Research Center of Elements Science, Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Abstract:
The iron-catalyzed Suzuki-Miyaura cross-coupling of secondary propargyl electrophiles with lithium organoborates has been established. A propyl-bridged bulky bisphosphine ligand, SciPROP-TB, cooperated with the bulky TIPS substituent at the alkyne terminal position to achieve the cross-coupling reaction with exclusive propargylic selectivity. The reaction features high functional group compatibility, regioselectivity, and yield with a broad substrate scope. The reaction of an optically active chiral propargyl bromide proceeds with complete racemization, supporting a mechanism involving propargyl radical formation.
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