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

Katie M J 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

Katie M J Feeney
, Guillaume Berionni
, Herbert Mayr^*
, Varinder K. Aggarwal

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

34 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2614-2617
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b00918
Publication status	Published - 5 Jun 2015

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title = "Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters",

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 = "Feeney, \{Katie M J\} and Guillaume Berionni and Herbert Mayr and Aggarwal, \{Varinder K.\}",

year = "2015",

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doi = "10.1021/acs.orglett.5b00918",

language = "English",

volume = "17",

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journal = "Organic Letters",

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T1 - Structure and reactivity of boron-ate complexes derived from primary and secondary boronic esters

AU - Feeney, Katie M J

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.

UR - https://www.scopus.com/pages/publications/84930620981

U2 - 10.1021/acs.orglett.5b00918

DO - 10.1021/acs.orglett.5b00918

M3 - Article (Academic Journal)

C2 - 25973673

AN - SCOPUS:84930620981

SN - 1523-7060

VL - 17

SP - 2614

EP - 2617

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

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

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

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