Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates
Publication type: Journal Article
Publication date: 2017-08-18
scimago Q1
wos Q1
SJR: 5.550
CiteScore: 27.6
Impact factor: 16.9
ISSN: 14337851, 15213773
PubMed ID:
28703388
General Chemistry
Catalysis
Abstract
This work showcases a new catalytic cyclization reaction using a highly Lewis acidic borane with concomitant C−H or C−C bond formation. The activation of alkyne‐containing substrates with B(C6F5)3 enabled the first catalytic intramolecular cyclizations of carboxylic acid substrates using this Lewis acid. In addition, intramolecular cyclizations of esters enable C−C bond formation as catalytic B(C6F5)3 can be used to effect formal 1,5‐alkyl migrations from the ester functional groups to unsaturated carbon–carbon frameworks. This metal‐free method was used for the catalytic formation of complex dihydropyrones and isocoumarins in very good yields under relatively mild conditions with excellent atom efficiency.
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49
Total citations:
49
Citations from 2024:
5
(10.2%)
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GOST
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Soltani Y., Wilkins L. C., Melen R. L. Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 39. pp. 11995-11999.
GOST all authors (up to 50)
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Soltani Y., Wilkins L. C., Melen R. L. Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates // Angewandte Chemie - International Edition. 2017. Vol. 56. No. 39. pp. 11995-11999.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201704789
UR - https://onlinelibrary.wiley.com/doi/10.1002/anie.201704789
TI - Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates
T2 - Angewandte Chemie - International Edition
AU - Soltani, Yashar
AU - Wilkins, Lewis C.
AU - Melen, Rebecca L.
PY - 2017
DA - 2017/08/18
PB - Wiley
SP - 11995-11999
IS - 39
VL - 56
PMID - 28703388
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Soltani,
author = {Yashar Soltani and Lewis C. Wilkins and Rebecca L. Melen},
title = {Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates},
journal = {Angewandte Chemie - International Edition},
year = {2017},
volume = {56},
publisher = {Wiley},
month = {aug},
url = {https://onlinelibrary.wiley.com/doi/10.1002/anie.201704789},
number = {39},
pages = {11995--11999},
doi = {10.1002/anie.201704789}
}
Cite this
MLA
Copy
Soltani, Yashar, et al. “Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C6F5)3 via Cationic Intermediates.” Angewandte Chemie - International Edition, vol. 56, no. 39, Aug. 2017, pp. 11995-11999. https://onlinelibrary.wiley.com/doi/10.1002/anie.201704789.