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Copper-Catalyzed trans-Hydroboration of Terminal Aryl Alkynes: Stereodivergent Synthesis of Alkenylboron Compounds.
- Source :
-
Organic letters [Org Lett] 2016 Mar 18; Vol. 18 (6), pp. 1390-3. Date of Electronic Publication: 2016 Mar 03. - Publication Year :
- 2016
-
Abstract
- 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-hydroborations.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 18
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 26936313
- Full Text :
- https://doi.org/10.1021/acs.orglett.6b00325