Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation

Jongwook Choi, David Y. Wang, Sabuj Kundu, Yuriy Choliy, Thomas J. Emge, Karsten Krogh-Jespersen, Alan S Goldman

Research output: Contribution to journalArticle

112 Citations (Scopus)

Abstract

Carbon-fluorine bonds are the strongest known single bonds to carbon and as a consequence can prove very hard to cleave. Alhough vinyl and aryl C-F bonds can undergo oxidative addition to transition metal complexes, this reaction has appeared inoperable with aliphatic substrates. We report the addition of C(sp3)-F bonds (including alkyl-F) to an iridium center via the initial, reversible cleavage of a C-H bond. These results suggest a distinct strategy for the development of catalysts and promoters to make and break C-F bonds, which are of strong interest in the context of both pharmaceutical and environmental chemistry.

Original languageEnglish
Pages (from-to)1545-1548
Number of pages4
JournalScience
Volume332
Issue number6037
DOIs
Publication statusPublished - Jun 24 2011

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Iridium
Carbon
Fluorine
Pharmaceutical Chemistry
Coordination Complexes
single bond

ASJC Scopus subject areas

  • General

Cite this

Choi, J., Wang, D. Y., Kundu, S., Choliy, Y., Emge, T. J., Krogh-Jespersen, K., & Goldman, A. S. (2011). Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation. Science, 332(6037), 1545-1548. https://doi.org/10.1126/science.1200514

Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation. / Choi, Jongwook; Wang, David Y.; Kundu, Sabuj; Choliy, Yuriy; Emge, Thomas J.; Krogh-Jespersen, Karsten; Goldman, Alan S.

In: Science, Vol. 332, No. 6037, 24.06.2011, p. 1545-1548.

Research output: Contribution to journalArticle

Choi, J, Wang, DY, Kundu, S, Choliy, Y, Emge, TJ, Krogh-Jespersen, K & Goldman, AS 2011, 'Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation', Science, vol. 332, no. 6037, pp. 1545-1548. https://doi.org/10.1126/science.1200514
Choi J, Wang DY, Kundu S, Choliy Y, Emge TJ, Krogh-Jespersen K et al. Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation. Science. 2011 Jun 24;332(6037):1545-1548. https://doi.org/10.1126/science.1200514
Choi, Jongwook ; Wang, David Y. ; Kundu, Sabuj ; Choliy, Yuriy ; Emge, Thomas J. ; Krogh-Jespersen, Karsten ; Goldman, Alan S. / Net oxidative addition of C(sp3)-F bonds to iridium via initial C-H bond activation. In: Science. 2011 ; Vol. 332, No. 6037. pp. 1545-1548.
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