Catecholborane (1, 3, 2-Benzodioxaborole). A Versatile Reducing Agent

George Kabalka, John D. Baker, Gary W. Neal

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

The reaction of 1, 3, 2-benzodioxaborole [catecholborane (CB)] with representative functional groups was studied to determine the utility of CB as a selective reducing agent. The approximate rates, stoichiometry, and products of the reductions were determined under standard conditions (CHCI3, 25 °C). The results indicate that CB is unique compared to other substituted boranes. The reduction rates appear to be solvent independent with the exception of alkenes. Primary alkenes react very sluggishly, whereas secondary alkenes are unreactive at room temperature; as a resuit, many selective reductions can be performed in the presence of alkenes.

Original languageEnglish (US)
Pages (from-to)512-517
Number of pages6
JournalJournal of Organic Chemistry
Volume42
Issue number3
DOIs
StatePublished - Jan 1 1977

Fingerprint

Reducing Agents
Alkenes
Boranes
Stoichiometry
Functional groups
Temperature

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Catecholborane (1, 3, 2-Benzodioxaborole). A Versatile Reducing Agent. / Kabalka, George; Baker, John D.; Neal, Gary W.

In: Journal of Organic Chemistry, Vol. 42, No. 3, 01.01.1977, p. 512-517.

Research output: Contribution to journalArticle

Kabalka, George ; Baker, John D. ; Neal, Gary W. / Catecholborane (1, 3, 2-Benzodioxaborole). A Versatile Reducing Agent. In: Journal of Organic Chemistry. 1977 ; Vol. 42, No. 3. pp. 512-517.
@article{06ccca1c57ac463d9b347b089120b439,
title = "Catecholborane (1, 3, 2-Benzodioxaborole). A Versatile Reducing Agent",
abstract = "The reaction of 1, 3, 2-benzodioxaborole [catecholborane (CB)] with representative functional groups was studied to determine the utility of CB as a selective reducing agent. The approximate rates, stoichiometry, and products of the reductions were determined under standard conditions (CHCI3, 25 °C). The results indicate that CB is unique compared to other substituted boranes. The reduction rates appear to be solvent independent with the exception of alkenes. Primary alkenes react very sluggishly, whereas secondary alkenes are unreactive at room temperature; as a resuit, many selective reductions can be performed in the presence of alkenes.",
author = "George Kabalka and Baker, {John D.} and Neal, {Gary W.}",
year = "1977",
month = "1",
day = "1",
doi = "10.1021/jo00423a025",
language = "English (US)",
volume = "42",
pages = "512--517",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Catecholborane (1, 3, 2-Benzodioxaborole). A Versatile Reducing Agent

AU - Kabalka, George

AU - Baker, John D.

AU - Neal, Gary W.

PY - 1977/1/1

Y1 - 1977/1/1

N2 - The reaction of 1, 3, 2-benzodioxaborole [catecholborane (CB)] with representative functional groups was studied to determine the utility of CB as a selective reducing agent. The approximate rates, stoichiometry, and products of the reductions were determined under standard conditions (CHCI3, 25 °C). The results indicate that CB is unique compared to other substituted boranes. The reduction rates appear to be solvent independent with the exception of alkenes. Primary alkenes react very sluggishly, whereas secondary alkenes are unreactive at room temperature; as a resuit, many selective reductions can be performed in the presence of alkenes.

AB - The reaction of 1, 3, 2-benzodioxaborole [catecholborane (CB)] with representative functional groups was studied to determine the utility of CB as a selective reducing agent. The approximate rates, stoichiometry, and products of the reductions were determined under standard conditions (CHCI3, 25 °C). The results indicate that CB is unique compared to other substituted boranes. The reduction rates appear to be solvent independent with the exception of alkenes. Primary alkenes react very sluggishly, whereas secondary alkenes are unreactive at room temperature; as a resuit, many selective reductions can be performed in the presence of alkenes.

UR - http://www.scopus.com/inward/record.url?scp=0001292168&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001292168&partnerID=8YFLogxK

U2 - 10.1021/jo00423a025

DO - 10.1021/jo00423a025

M3 - Article

VL - 42

SP - 512

EP - 517

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -