Copper-Catalyzed trans-Hydroboration of Terminal Aryl Alkynes: Stereodivergent Synthesis of Alkenylboron Compounds

Won Jun Jang, Woo Lim Lee, Jong Hun Moon, Jin Yong Lee, Jaesook Yun

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110 Scopus citations

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.

Original languageEnglish
Pages (from-to)1390-1393
Number of pages4
JournalOrganic Letters
Volume18
Issue number6
DOIs
StatePublished - 18 Mar 2016

Bibliographical note

Publisher Copyright:
© 2016 American Chemical Society.

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