The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity
Publication type: Journal Article
Publication date: 2015-09-03
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
26335721
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.
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60
Total citations:
60
Citations from 2025:
1
(1.67%)
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Morri A. K. et al. The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity // Organic Letters. 2015. Vol. 17. No. 18. pp. 4640-4643.
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Morri A. K., Thummala Y., Doddi V. R. The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity // Organic Letters. 2015. Vol. 17. No. 18. pp. 4640-4643.
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TY - JOUR
DO - 10.1021/acs.orglett.5b02398
UR - https://doi.org/10.1021/acs.orglett.5b02398
TI - The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity
T2 - Organic Letters
AU - Morri, Ashok Kumar
AU - Thummala, Yadagiri
AU - Doddi, Venkata Ramana
PY - 2015
DA - 2015/09/03
PB - American Chemical Society (ACS)
SP - 4640-4643
IS - 18
VL - 17
PMID - 26335721
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2015_Morri,
author = {Ashok Kumar Morri and Yadagiri Thummala and Venkata Ramana Doddi},
title = {The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity},
journal = {Organic Letters},
year = {2015},
volume = {17},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.orglett.5b02398},
number = {18},
pages = {4640--4643},
doi = {10.1021/acs.orglett.5b02398}
}
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MLA
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Morri, Ashok Kumar, et al. “The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity.” Organic Letters, vol. 17, no. 18, Sep. 2015, pp. 4640-4643. https://doi.org/10.1021/acs.orglett.5b02398.