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Highly regio-and stereoselective preparation of Z-vinylboronates by a formal trans-hydroboration of terminal alkynes

delete2026-03-01
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PRE
AI
A
Arianna Serrano
J
Jonathan L. Kuo
B
Boon, Byron A.
M
Merlic, Craig A.
I
Iafe, Robert G. *
DOI:10.1016/j.tetlet.2026.156055delete
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Abstract

Abstract

En 中文
We report an operationally convenient process for the preparation of Z-vinylboronates from terminal alkynes via a hydrozirconation/protonation procedure of in situ-generated 1-alkynylboronates with in situ-generated Schwartz's reagent (HCp2ZrCl). 1-Alkynylboronates are generated via reaction of lithiated alkynes with isopropyl pinacol borate, and Schwartz's reagent is generated conveniently by the slow reduction of ZrCp2Cl2 with diisobutylaluminum hydride (DIBAL-H) at room temperature.
Keywords:
Trans-hydroboration
cis pinacol vinylboronate
cis-alkenyl dioxaborolane
Schwartz's reagent
Z pinacol vinylboronate

Journal

T
Tetrahedron Letters
IF:
1.5
Papers:
148
Citations:
4.2W

Organization

California State University System cover
California State University System
Scholars:
2.7W
Papers: 2.4W
Citations: 457
C
California State University San Marcos
Scholars:
27
Papers: 20
Citations: 0
University of California System cover
University of California System
Scholars:
37.2W
Papers: 33.6W
Citations: 6.6K
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