Development of Organic Transformations Based on Protodeboronation

Chun Young Lee, Cheol-Hong Cheon

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Although protodeboronation has been considered as an uncontrollable side reaction in metal-catalyzed cross-coupling and/or a decomposition pathway of unstable organoboron compounds, the synthetic organic community has not recognized the importance of protodeboronation and the underlying mechanism, and thus few organic transformations have been developed based on the protodeboronation of organoboron compounds until recently. However, recently the synthetic community has started to understand the reactionmechanism and reaction parameters for protodeboronation, which enabled us to develop methods in which carbon-boron bonds in organoboron compounds can be converted into carbon-hydrogen bonds under mild conditions. Based on this finding several synthetic protocols have been developed recently. In this chapter, recent progress in the development of novel organic transformations based on protodeboronation will be described.

Original languageEnglish
Title of host publicationBoron Reagents in Synthesis
PublisherAmerican Chemical Society
Pages483-523
Number of pages41
Volume1236
ISBN (Electronic)9780841231832
DOIs
Publication statusPublished - 2016

Publication series

NameACS Symposium Series
Volume1236
ISSN (Print)00976156
ISSN (Electronic)19475918

Fingerprint

Carbon
Boron
Hydrogen bonds
Metals
Decomposition

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Lee, C. Y., & Cheon, C-H. (2016). Development of Organic Transformations Based on Protodeboronation. In Boron Reagents in Synthesis (Vol. 1236, pp. 483-523). (ACS Symposium Series; Vol. 1236). American Chemical Society. https://doi.org/10.1021/bk-2016-1236.ch015

Development of Organic Transformations Based on Protodeboronation. / Lee, Chun Young; Cheon, Cheol-Hong.

Boron Reagents in Synthesis. Vol. 1236 American Chemical Society, 2016. p. 483-523 (ACS Symposium Series; Vol. 1236).

Research output: Chapter in Book/Report/Conference proceedingChapter

Lee, CY & Cheon, C-H 2016, Development of Organic Transformations Based on Protodeboronation. in Boron Reagents in Synthesis. vol. 1236, ACS Symposium Series, vol. 1236, American Chemical Society, pp. 483-523. https://doi.org/10.1021/bk-2016-1236.ch015
Lee CY, Cheon C-H. Development of Organic Transformations Based on Protodeboronation. In Boron Reagents in Synthesis. Vol. 1236. American Chemical Society. 2016. p. 483-523. (ACS Symposium Series). https://doi.org/10.1021/bk-2016-1236.ch015
Lee, Chun Young ; Cheon, Cheol-Hong. / Development of Organic Transformations Based on Protodeboronation. Boron Reagents in Synthesis. Vol. 1236 American Chemical Society, 2016. pp. 483-523 (ACS Symposium Series).
@inbook{13e757c11a0b458288c3663d2193c4b3,
title = "Development of Organic Transformations Based on Protodeboronation",
abstract = "Although protodeboronation has been considered as an uncontrollable side reaction in metal-catalyzed cross-coupling and/or a decomposition pathway of unstable organoboron compounds, the synthetic organic community has not recognized the importance of protodeboronation and the underlying mechanism, and thus few organic transformations have been developed based on the protodeboronation of organoboron compounds until recently. However, recently the synthetic community has started to understand the reactionmechanism and reaction parameters for protodeboronation, which enabled us to develop methods in which carbon-boron bonds in organoboron compounds can be converted into carbon-hydrogen bonds under mild conditions. Based on this finding several synthetic protocols have been developed recently. In this chapter, recent progress in the development of novel organic transformations based on protodeboronation will be described.",
author = "Lee, {Chun Young} and Cheol-Hong Cheon",
year = "2016",
doi = "10.1021/bk-2016-1236.ch015",
language = "English",
volume = "1236",
series = "ACS Symposium Series",
publisher = "American Chemical Society",
pages = "483--523",
booktitle = "Boron Reagents in Synthesis",

}

TY - CHAP

T1 - Development of Organic Transformations Based on Protodeboronation

AU - Lee, Chun Young

AU - Cheon, Cheol-Hong

PY - 2016

Y1 - 2016

N2 - Although protodeboronation has been considered as an uncontrollable side reaction in metal-catalyzed cross-coupling and/or a decomposition pathway of unstable organoboron compounds, the synthetic organic community has not recognized the importance of protodeboronation and the underlying mechanism, and thus few organic transformations have been developed based on the protodeboronation of organoboron compounds until recently. However, recently the synthetic community has started to understand the reactionmechanism and reaction parameters for protodeboronation, which enabled us to develop methods in which carbon-boron bonds in organoboron compounds can be converted into carbon-hydrogen bonds under mild conditions. Based on this finding several synthetic protocols have been developed recently. In this chapter, recent progress in the development of novel organic transformations based on protodeboronation will be described.

AB - Although protodeboronation has been considered as an uncontrollable side reaction in metal-catalyzed cross-coupling and/or a decomposition pathway of unstable organoboron compounds, the synthetic organic community has not recognized the importance of protodeboronation and the underlying mechanism, and thus few organic transformations have been developed based on the protodeboronation of organoboron compounds until recently. However, recently the synthetic community has started to understand the reactionmechanism and reaction parameters for protodeboronation, which enabled us to develop methods in which carbon-boron bonds in organoboron compounds can be converted into carbon-hydrogen bonds under mild conditions. Based on this finding several synthetic protocols have been developed recently. In this chapter, recent progress in the development of novel organic transformations based on protodeboronation will be described.

UR - http://www.scopus.com/inward/record.url?scp=85005950406&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85005950406&partnerID=8YFLogxK

U2 - 10.1021/bk-2016-1236.ch015

DO - 10.1021/bk-2016-1236.ch015

M3 - Chapter

AN - SCOPUS:85005950406

VL - 1236

T3 - ACS Symposium Series

SP - 483

EP - 523

BT - Boron Reagents in Synthesis

PB - American Chemical Society

ER -