Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters

Kathryn Feeney; Guillaume Berionni; Herbert Mayr; Varinder K. Aggarwal

doi:10.1021/acs.orglett.5b00918

Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters

Kathryn Feeney, Guillaume Berionni, Herbert Mayr, Varinder K. Aggarwal

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Résumé

Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.

langue originale	Anglais
Pages (de - à)	2614-2617
Nombre de pages	4
journal	Organic Letters
Volume	17
Numéro de publication	11
Les DOIs	https://doi.org/10.1021/acs.orglett.5b00918
Etat de la publication	Publié - 5 juin 2015
Modification externe	Oui

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10.1021/acs.orglett.5b00918

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abstract = "Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.",

author = "Kathryn Feeney and Guillaume Berionni and Herbert Mayr and Aggarwal, {Varinder K.}",

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AU - Feeney, Kathryn

AU - Berionni, Guillaume

AU - Mayr, Herbert

AU - Aggarwal, Varinder K.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.

AB - Boron-ate complexes derived from primary and secondary boronic esters and aryllithiums have been isolated, and the kinetics of their reactions with carbenium ions studied. The second-order rate constants have been used to derive nucleophilicity parameters for the boron-ate complexes, revealing that nucleophilicity increased with (i) electron-donating aromatics on boron, (ii) neopentyl glycol over pinacol boronic esters, and (iii) 12-crown-4 ether.

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SP - 2614

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JO - Organic Letters

JF - Organic Letters

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ER -

Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters

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