Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds

Ziyuan Pang; Xin Wen; Yuhang Qiao; Xiaoli Ma; Zhi Yang

doi:10.1134/S1070428025604972

Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds

Ziyuan Pang
, Xin Wen
, Yuhang Qiao
, Xiaoli Ma^*
, Zhi Yang^*

^*Corresponding author for this work

Beijing Institute of Technology
Ltd.

Research output: Contribution to journal › Article › peer-review

Abstract

Abstract: The use of two economically viable and environmentally benign nonprecious-metal organozinc complexes as catalysts for the hydrostannation of terminal alkynes has been reported. Commercially available ZnEt₂ and a laboratory-prepared β-diketiminate ethylzinc complex LZnEt [L = HC(CMeNAr)₂, Ar = 2,6-(i-Pr)₂C₆H₃] exhibit excellent catalytic efficiency in the hydrostannation of terminal alkynes with Bu₃SnH, showing a broad substrate scope across aromatic, aliphatic, and alicyclic derivatives. Notably, ZnEt₂ demonstrates slightly higher catalytic activity than LZnEt, whereas the sterically demanding complex LZnEt provides enhanced stereoselectivity, which is attributed to its greater steric hindrance. A plausible mechanism for the ZnEt₂-catalyzed stannylation of terminal alkynes is proposed based on key reaction intermediates characterized by NMR spectroscopy.

Original language	English
Article number	129
Journal	Russian Journal of Organic Chemistry
Volume	62
Issue number	6
DOIs	https://doi.org/10.1134/S1070428025604972
Publication status	Published - Jun 2026
Externally published	Yes

Keywords

organozinc compounds
stannylation
terminal alkynes

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10.1134/S1070428025604972

Cite this

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title = "Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds",

abstract = "Abstract: The use of two economically viable and environmentally benign nonprecious-metal organozinc complexes as catalysts for the hydrostannation of terminal alkynes has been reported. Commercially available ZnEt2 and a laboratory-prepared β-diketiminate ethylzinc complex LZnEt [L = HC(CMeNAr)2, Ar = 2,6-(i-Pr)2C6H3] exhibit excellent catalytic efficiency in the hydrostannation of terminal alkynes with Bu3SnH, showing a broad substrate scope across aromatic, aliphatic, and alicyclic derivatives. Notably, ZnEt2 demonstrates slightly higher catalytic activity than LZnEt, whereas the sterically demanding complex LZnEt provides enhanced stereoselectivity, which is attributed to its greater steric hindrance. A plausible mechanism for the ZnEt2-catalyzed stannylation of terminal alkynes is proposed based on key reaction intermediates characterized by NMR spectroscopy.",

keywords = "organozinc compounds, stannylation, terminal alkynes",

author = "Ziyuan Pang and Xin Wen and Yuhang Qiao and Xiaoli Ma and Zhi Yang",

note = "Publisher Copyright: {\textcopyright} Pleiades Publishing, Ltd. 2026.",

year = "2026",

month = jun,

doi = "10.1134/S1070428025604972",

language = "English",

volume = "62",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "Pleiades Publishing",

number = "6",

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TY - JOUR

T1 - Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds

AU - Pang, Ziyuan

AU - Wen, Xin

AU - Qiao, Yuhang

AU - Ma, Xiaoli

AU - Yang, Zhi

N1 - Publisher Copyright: © Pleiades Publishing, Ltd. 2026.

PY - 2026/6

Y1 - 2026/6

N2 - Abstract: The use of two economically viable and environmentally benign nonprecious-metal organozinc complexes as catalysts for the hydrostannation of terminal alkynes has been reported. Commercially available ZnEt2 and a laboratory-prepared β-diketiminate ethylzinc complex LZnEt [L = HC(CMeNAr)2, Ar = 2,6-(i-Pr)2C6H3] exhibit excellent catalytic efficiency in the hydrostannation of terminal alkynes with Bu3SnH, showing a broad substrate scope across aromatic, aliphatic, and alicyclic derivatives. Notably, ZnEt2 demonstrates slightly higher catalytic activity than LZnEt, whereas the sterically demanding complex LZnEt provides enhanced stereoselectivity, which is attributed to its greater steric hindrance. A plausible mechanism for the ZnEt2-catalyzed stannylation of terminal alkynes is proposed based on key reaction intermediates characterized by NMR spectroscopy.

AB - Abstract: The use of two economically viable and environmentally benign nonprecious-metal organozinc complexes as catalysts for the hydrostannation of terminal alkynes has been reported. Commercially available ZnEt2 and a laboratory-prepared β-diketiminate ethylzinc complex LZnEt [L = HC(CMeNAr)2, Ar = 2,6-(i-Pr)2C6H3] exhibit excellent catalytic efficiency in the hydrostannation of terminal alkynes with Bu3SnH, showing a broad substrate scope across aromatic, aliphatic, and alicyclic derivatives. Notably, ZnEt2 demonstrates slightly higher catalytic activity than LZnEt, whereas the sterically demanding complex LZnEt provides enhanced stereoselectivity, which is attributed to its greater steric hindrance. A plausible mechanism for the ZnEt2-catalyzed stannylation of terminal alkynes is proposed based on key reaction intermediates characterized by NMR spectroscopy.

KW - organozinc compounds

KW - stannylation

KW - terminal alkynes

UR - https://www.scopus.com/pages/publications/105050554540

U2 - 10.1134/S1070428025604972

DO - 10.1134/S1070428025604972

M3 - Article

AN - SCOPUS:105050554540

SN - 1070-4280

VL - 62

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

IS - 6

M1 - 129

ER -

Hydrostannation of Terminal Alkynes Catalyzed by Organozinc Compounds

Abstract

Keywords

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