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Process for the functionalization of heteroalkanes and arenes

A technology for functionalization and heteroalkane, which is applied in the field of functionalization of heteroalkane and aromatics, and can solve problems such as low selectivity

Inactive Publication Date: 2017-05-17
THE SCRIPPS RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct methods are challenging because the functionalization of arenes such as benzene often involves low selectivities

Method used

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  • Process for the functionalization of heteroalkanes and arenes
  • Process for the functionalization of heteroalkanes and arenes
  • Process for the functionalization of heteroalkanes and arenes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] This example illustrates the use of an oxidative electrophile comprising an oxidized form of a main group element to activate and functionalize the C-H bond of an arenebenzene.

[0168]found C. 6 f 5 I (+3) (TFA) 2 (1) Effectively used for selective monofunctionalization of benzene (PhH) to PhTFA at lower temperature (125 °C). Lowering the temperature of the reaction to 100 °C resulted in complete consumption of 1 and production of new species in solution, which was passed through 1 H-and 19 Preliminary identification by F-NMR of diaryl-λ 3 -Iodine [C 6 f 5 -I III -C 6 h 5 ][TFA](3), and only trace amounts of PhTFA and C 6 f 5 -I I (2). Further heating of the solution at 125 °C resulted in complete conversion of 3 to PhTFA and 2. This observation is consistent with the role of 3 as an intermediate in the conversion of PhH to PhTFA (Scheme 7).

[0169] Option 7

[0170]

Embodiment 2

[0172] This example illustrates the use of an oxidizing electrophile comprising an oxidized form of a main group element to activate and functionalize the C-H bond of the arene toluene.

[0173] Toluene and C 6 f 5 I (+3) (TFA) 2 (1) Reactivity. Using standard reaction conditions (eg 3h, 150°C), p-MeC was observed 6 h 4 TFA and o-MeC 6 h 4 TFA was produced quantitatively in an approximately 3:1 ratio (based on starting [1]); and did not form any benzylic oxygen functionalized product as expected from a free radical route (Scheme 8).

[0174] Option 8

[0175]

[0176] Clearly, relative to the methyl sp 3 - Functionalization of hybridized carbon atoms, sp of aryl rings 2 - Functionalization of hybridized carbon atoms is advantageous.

Embodiment 3

[0178] This example illustrates the use of an oxidative electrophile comprising an oxidized form of a main group element to activate and functionalize the C-H bond of an arenebenzene.

[0179] Make Pb(TFA) at 25°C 4 Reaction with benzene (PhH) in trifluoroacetic acid (TFAH) afforded the selectively monofunctionalized product PhTFA in 80% yield (Scheme 9). The reaction is very easy as the reaction occurs almost instantly at room temperature.

[0180] Option 9

[0181]

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Abstract

Provided are methods and materials for the functionalization of a heteroalkane or arene using an oxidizing electrophile as a stoichiometric agent or catalyst. The reaction involves the replacement of a hydrogen atom on an sp3-hybridized carbon atom of the heteroalkane or of a hydrogen atom on an sp2-hybridized carbon atom of the arene. A main group element organometallic intermediate is formed that undergoes further conversion to a functionalized heteroalkane or arene.

Description

[0001] Cross References to Related Applications [0002] This patent application claims the benefit of U.S. Provisional Patent Application No. 62 / 042,101, filed August 26, 2014, and U.S. Provisional Patent Application No. 62 / 041,270, filed August 25, 2014, the entire contents of which are incorporated by reference The full text is provided by reference. [0003] Statement Regarding Federally Funded Research and Development [0004] This invention was made with government support under GQ10044-133945 awarded by the US Department of Energy. The government has certain rights in this invention. [0005] Background of the invention [0006] An important approach that has emerged in the past few decades is the design of molecular (homogeneous) catalysts or reagents for the oxidative functionalization of hydrocarbons based on C–H activation reactions. This involves reacting a regenerable M–X catalyst or reagent (M is a main group element in the oxidized state; X is one or more char...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/54C07C71/00C07C53/18C07C69/63C07C67/035C07C67/05C07C67/12
CPCC07C51/54C07C67/035C07C67/05C07C67/12C07C71/00C07C53/18C07C69/63Y02P20/582Y02P20/52C07C29/48C07C29/72C07C67/055C07C2523/08C07C2523/14C07C2523/16C07C2523/70
Inventor R·佩里亚纳M·肯尼克B·哈士古驰
Owner THE SCRIPPS RES INST
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