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

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

25 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

Structured keywords

BCS and TECS CDTs

Access to Document

10.1021/acs.orglett.5b00918

Handle.net

Persistent link

Cite this

@article{48499e8cb7294cfe8395e7fdd12166d9,

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",

month = jun,

day = "5",

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

language = "English",

volume = "17",

pages = "2614--2617",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=84930620981&partnerID=8YFLogxK

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

Abstract

Structured keywords

Access to Document

Handle.net

Other files and links

Fingerprint

3-month Core Capability for Chemistry Research

Cite this

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

Abstract

Structured keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

3-month Core Capability for Chemistry Research

Cite this