Evidence for the Formation of Acylboronate Intermediates in the Carbonylation Reactions of Organoboranes

George Kabalka, J. Timothy Gotsick, R. David Pace, Nan Sheng Li

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion.

Original languageEnglish (US)
Pages (from-to)5163-5165
Number of pages3
JournalOrganometallics
Volume13
Issue number12
DOIs
StatePublished - Dec 1 1994
Externally publishedYes

Fingerprint

Carbonylation
Carbon Monoxide
Ketones
ketones
carbon monoxide
reagents
hydrogen peroxide
Hydrogen Peroxide
Anions
anions
Oxidation
oxidation

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Evidence for the Formation of Acylboronate Intermediates in the Carbonylation Reactions of Organoboranes. / Kabalka, George; Gotsick, J. Timothy; Pace, R. David; Li, Nan Sheng.

In: Organometallics, Vol. 13, No. 12, 01.12.1994, p. 5163-5165.

Research output: Contribution to journalArticle

Kabalka, George ; Gotsick, J. Timothy ; Pace, R. David ; Li, Nan Sheng. / Evidence for the Formation of Acylboronate Intermediates in the Carbonylation Reactions of Organoboranes. In: Organometallics. 1994 ; Vol. 13, No. 12. pp. 5163-5165.
@article{0d21f32169164baa8a962c18d1092bfa,
title = "Evidence for the Formation of Acylboronate Intermediates in the Carbonylation Reactions of Organoboranes",
abstract = "Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion.",
author = "George Kabalka and Gotsick, {J. Timothy} and Pace, {R. David} and Li, {Nan Sheng}",
year = "1994",
month = "12",
day = "1",
doi = "10.1021/om00024a069",
language = "English (US)",
volume = "13",
pages = "5163--5165",
journal = "Organometallics",
issn = "0276-7333",
publisher = "American Chemical Society",
number = "12",

}

TY - JOUR

T1 - Evidence for the Formation of Acylboronate Intermediates in the Carbonylation Reactions of Organoboranes

AU - Kabalka, George

AU - Gotsick, J. Timothy

AU - Pace, R. David

AU - Li, Nan Sheng

PY - 1994/12/1

Y1 - 1994/12/1

N2 - Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion.

AB - Trialkylboranes react with acyllithium reagents to yield ketones after oxidation with hydrogen peroxide. The ketones contain one alkyl group supplied by the alkyllithium reagent and one alkyl group supplied by the organoborane. The experimental results support the hypothesis that an acylboronate is an intermediate in the reactions of organoboranes with carbon monoxide. The yields are modest due to an apparent competition between carbon monoxide and organoborane for the alkyllithium needed to generate the acyl anion.

UR - http://www.scopus.com/inward/record.url?scp=0028732979&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028732979&partnerID=8YFLogxK

U2 - 10.1021/om00024a069

DO - 10.1021/om00024a069

M3 - Article

VL - 13

SP - 5163

EP - 5165

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 12

ER -