Angewandte Chemie - International Edition

, том 56 , издание 39 , страницы 11995-11999

Stoichiometric and Catalytic C−C and C−H Bond Formation with B(C₆F₅)₃ via Cationic Intermediates

Тип публикации: Journal Article

Дата публикации: 2017-08-18

Wiley

Angewandte Chemie - International Edition

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SJR: 5.55

CiteScore: 27.6

Impact factor: 16.9

ISSN: 14337851, 15213773

DOI: 10.1002/anie.201704789

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PubMed ID: 28703388

General Chemistry

Catalysis

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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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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.

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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 -

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@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}

}

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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.