Journal
ORGANIC LETTERS
Volume 18, Issue 6, Pages 1390-1393Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00325
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Funding
- Basic Science Research Program through the National Research Foundation of Korea (NRF) - Ministry of Education, Science, and Technology [NRF-2013R1A1A2058160]
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A Cu-catalyzed highly Z-stereoselective hydroboration of alkynes with 1,8-naphthalenediaminatoborane (HB(dan)) is developed. DPEphos (bis[(2-diphenylphosphino)phenyl] ether)-ligated Cu catalysts produced alkenylboron compounds from terminal alkynes with excellent Z-stereoselectivity. In contrast, using a SIPr-CuCl complex as the precatalyst exclusively produced E-hydroboration products at mild conditions. Both catalytic procedures form alkenylboron products stereocomplementary to each other, constituting stereodivergent hydroboration of alkynes through Cu catalysis. Deuterium labeling and isomerization studies support the Z-selective hydroboration via trans-addition of the boron reagent to terminal alkynes as opposed to precedent noble-metal-catalyzed trans-hydroboration.
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