Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates

Ajdin Kavara, Michael M. Kheir, Jeff W. Kampf, Mark M. Banaszak Holl

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Using the radical cyclization induced by the reaction of [InlineMediaObject not available: see fulltext.] (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C–H activation to be 1.1 ± 0.2 × 108 M−1 s−1. The rate of oxidative addition of aryl halide with 1 was estimated to be 107–108 M−1 s−1. The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 × 109 s−1) is faster than the rate of hydrocarbon/alkene/alkyne C–H abstraction.

Original languageEnglish
Pages (from-to)250-257
Number of pages8
JournalJournal of Inorganic and Organometallic Polymers and Materials
Volume24
Issue number1
DOIs
Publication statusPublished - 1 Jan 2014
Externally publishedYes

Keywords

  • C–H activation
  • Radical clock
  • Stannylene

Cite this

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title = "Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates",
abstract = "Using the radical cyclization induced by the reaction of [InlineMediaObject not available: see fulltext.] (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C–H activation to be 1.1 ± 0.2 × 108 M−1 s−1. The rate of oxidative addition of aryl halide with 1 was estimated to be 107–108 M−1 s−1. The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 × 109 s−1) is faster than the rate of hydrocarbon/alkene/alkyne C–H abstraction.",
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Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates. / Kavara, Ajdin; Kheir, Michael M.; Kampf, Jeff W.; Banaszak Holl, Mark M.

In: Journal of Inorganic and Organometallic Polymers and Materials, Vol. 24, No. 1, 01.01.2014, p. 250-257.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates

AU - Kavara, Ajdin

AU - Kheir, Michael M.

AU - Kampf, Jeff W.

AU - Banaszak Holl, Mark M.

PY - 2014/1/1

Y1 - 2014/1/1

N2 - Using the radical cyclization induced by the reaction of [InlineMediaObject not available: see fulltext.] (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C–H activation to be 1.1 ± 0.2 × 108 M−1 s−1. The rate of oxidative addition of aryl halide with 1 was estimated to be 107–108 M−1 s−1. The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 × 109 s−1) is faster than the rate of hydrocarbon/alkene/alkyne C–H abstraction.

AB - Using the radical cyclization induced by the reaction of [InlineMediaObject not available: see fulltext.] (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C–H activation to be 1.1 ± 0.2 × 108 M−1 s−1. The rate of oxidative addition of aryl halide with 1 was estimated to be 107–108 M−1 s−1. The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 × 109 s−1) is faster than the rate of hydrocarbon/alkene/alkyne C–H abstraction.

KW - C–H activation

KW - Radical clock

KW - Stannylene

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