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Search for "counteranion activation" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

Pavel Nagorny and
Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds. Keywords: C–H hydrogen bond; counteranion activation; electrophile activation; halogen bond donor; hydrogen bond donor; organocatalysis; Review Introduction Over the past century chemists

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Graphical Abstract

Figure 1: Electrophile Activation by Hydrogen Bond Donors [1-16].

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Figure 2: Early examples of C–H hydrogen bonds and their recent use in supramolecular chemistry [18,19,32-34].

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Scheme 1: Design of 1,2,3-triazole-based catalysts for trityl group transfer through chloride anion binding b...

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Scheme 2: Examples of chiral triazole-based catalysts for anion activation designed by Mancheno and co-worker...

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Scheme 3: Application of chiral triazole-based catalysts L3 and L4 for counterion activation of pyridinium, q...

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Scheme 4: Ammonium salt anion binding via C–H hydrogen bonds in solid state [40-45,50,51].

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Scheme 5: Early examples of ammonium salts being used for electrophilic activation of imines in aza-Diels–Ald...

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Scheme 6: Ammonium salts as hydrogen bond-donor catalysts by Bibal and co-workers [53,54].

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Scheme 7: Tetraalkylammonium catalyst (L6)-catalyzed dearomatization of isoquinolinium salts [50].

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Scheme 8: Tetraalkylammonium catalyst L6 complexation to halogen-containing substrates [51].

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Scheme 9: Tetraalkylammonium-catalyzed aza-Diels–Alder reaction by Maruoka and co-workers [52].

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Scheme 10: (A) Alkylpyridinium catalysts L13-catalyzed reaction of 1-isochroman and silyl ketene acetals by Be...

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Scheme 11: Mixed N–H/C–H two hydrogen bond donors L14 and L15 as organocatalysts for ROP of lactide by Bibal a...

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Scheme 12: Examples of stable complexes based on halogen bonding [68,69].

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Scheme 13: Interaction between (−)-sparteine hydrobromide and (S)-1,2-dibromohexafluoropropane in the cocrysta...

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Scheme 14: Iodine-catalyzed reactions that are computationally proposed to proceed through halogen bond to car...

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Scheme 15: Transfer hydrogenation of phenylquinolines catalyzed by haloperfluoroalkanes by Bolm and co-workers ...

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Scheme 16: Halogen bond activation of benzhydryl bromides by Huber and co-workers [82].

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Scheme 17: Halogen bond-donor-catalyzed addition to oxocarbenium ions by Huber and co-workers [89].

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Scheme 18: Halogen bond-donor activation of α,β-unsaturated carbonyl compounds in the [2 + 4] cycloaddition re...

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Scheme 19: Halogen bond donor activation of imines in the [2 + 4] cycloaddition reaction of imine and Danishef...

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Scheme 20: Transfer hydrogenation catalyzed by a chiral halogen bond donor by Tan and co-workers [91].

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Scheme 21: Allylation of benzylic alcohols by Takemoto and co-workers [92].

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Scheme 22: NIS induced semipinacol rearrangement via C–X bond cleavage [93].

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Review

Published 23 Dec 2016

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