Zn(OTf)₂‐Catalyzed Dehydrocoupling of Terminal Alkynes with Diisopropylaminoborane: A Modular Route to Mono‐ and Dialkynylboranes
Abstract
The controlled incorporation of alkynyl groups onto boron centers is a powerful yet challenging transformation in organoboron chemistry, particularly for the synthesis of dialkynylboranes. Here, we report a modular and efficient strategy based on Zn(OTf)₂‐catalyzed dehydrocoupling of terminal alkynes with diisopropylaminoborane (DIPOB), enabling the selective formation of both mono‐ and dialkynylboranes under mild conditions. The use of DIPOB as a borylating agent offers fine‐tuned reactivity and suppresses undesired hydroboration side reactions. The resulting aminoboranes can be further converted into stable tetracoordinate boron complexes via ligand exchange to provide stable products. Mechanistic studies reveal a reversible alkyne addition step, offering insights into the dynamic behavior of these transformations. Overall, this work provides a practical and versatile platform for accessing an underexplored class of alkynylboron derivatives.
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BibTeX
@article{bequetermoy2026znotf₂catalyzed,
title = {{Zn(OTf)₂‐Catalyzed Dehydrocoupling of Terminal Alkynes with Diisopropylaminoborane: A Modular Route to Mono‐ and Dialkynylboranes}},
author = {Etienne Bequet-Ermoy and Nicolas Zivic and Laurent Chabaud and Mathieu Pucheault and Gabin Lalande},
journal = {Advanced Synthesis and Catalysis},
year = {2026},
month = oct,
doi = {10.1002/adsc.70504},
url = {https://hal.science/hal-05775189v1},
note = {CC BY-NC-ND 4.0},
}
RIS
TY - JOUR
TI - Zn(OTf)₂‐Catalyzed Dehydrocoupling of Terminal Alkynes with Diisopropylaminoborane: A Modular Route to Mono‐ and Dialkynylboranes
AU - Etienne Bequet-Ermoy
AU - Nicolas Zivic
AU - Laurent Chabaud
AU - Mathieu Pucheault
AU - Gabin Lalande
PY - 2026
DA - 2026/10/02
JO - Advanced Synthesis and Catalysis
DO - 10.1002/adsc.70504
UR - https://hal.science/hal-05775189v1
AB - The controlled incorporation of alkynyl groups onto boron centers is a powerful yet challenging transformation in organoboron chemistry, particularly for the synthesis of dialkynylboranes. Here, we report a modular and efficient strategy based on Zn(OTf)₂‐catalyzed dehydrocoupling of terminal alkynes with diisopropylaminoborane (DIPOB), enabling the selective formation of both mono‐ and dialkynylboranes under mild conditions. The use of DIPOB as a borylating agent offers fine‐tuned reactivity and suppresses undesired hydroboration side reactions. The resulting aminoboranes can be further converted into stable tetracoordinate boron complexes via ligand exchange to provide stable products. Mechanistic studies reveal a reversible alkyne addition step, offering insights into the dynamic behavior of these transformations. Overall, this work provides a practical and versatile platform for accessing an underexplored class of alkynylboron derivatives.
SN - 1615-4150
SN - 1615-4169
ER -