Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes
Wei Hao
1, 2
,
Yan Zhang
1, 2
,
Nan-Nan Wang
1, 2, 3, 4
,
Rong Fu
1, 2
,
Ke Chen
1, 2
,
Wen-Juan Hao
1, 2, 3, 4
,
Hao Wen
1, 2
,
Bo Jiang
1, 2, 3, 4
1
School of Chemistry & Materials Science, Xuzhou, China
|
3
School of Chemistry & Materials Science
Publication type: Journal Article
Publication date: 2025-03-17
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
Abstract
Instead of the conventional [4+2] cycloaddition, a regioselective Schmittel-type [2+2] cycloaddition of yne–allene esters, generated in situ from copper-catalyzed dediazotized coupling of γ-alkynyl diazoacetates with terminal alkynes, is reported, enabling a bicyclization process to produce a diverse array of C1-arylated cyclobuta[a]indenes in moderate to good yields. The protocol features wide functional group compatibility, mild reaction conditions, and experimental simplicity, holding significant potential for building new tricyclic cyclobutenes.
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Hao W. et al. Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes // Organic Letters. 2025. Vol. 27. No. 12. pp. 2941-2946.
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Hao W., Zhang Y., Wang N., Fu R., Chen K., Hao W., Wen H., Jiang B. Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes // Organic Letters. 2025. Vol. 27. No. 12. pp. 2941-2946.
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TY - JOUR
DO - 10.1021/acs.orglett.5c00525
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.5c00525
TI - Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes
T2 - Organic Letters
AU - Hao, Wei
AU - Zhang, Yan
AU - Wang, Nan-Nan
AU - Fu, Rong
AU - Chen, Ke
AU - Hao, Wen-Juan
AU - Wen, Hao
AU - Jiang, Bo
PY - 2025
DA - 2025/03/17
PB - American Chemical Society (ACS)
SP - 2941-2946
IS - 12
VL - 27
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2025_Hao,
author = {Wei Hao and Yan Zhang and Nan-Nan Wang and Rong Fu and Ke Chen and Wen-Juan Hao and Hao Wen and Bo Jiang},
title = {Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes},
journal = {Organic Letters},
year = {2025},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.5c00525},
number = {12},
pages = {2941--2946},
doi = {10.1021/acs.orglett.5c00525}
}
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Hao, Wei, et al. “Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes.” Organic Letters, vol. 27, no. 12, Mar. 2025, pp. 2941-2946. https://pubs.acs.org/doi/10.1021/acs.orglett.5c00525.