Acid-Catalyzed <i>ortho</i>-Alkylation of Anilines with Styrenes:  An Improved Route to Chiral Anilines with Bulky Substituents

Cherian, Anna E.; Domski, Gregory J.; Rose, Jeffrey M.; Lobkovsky, Emil; Coates, Geoffrey W.

doi:10.1021/ol051916j

Cited by 62 publications

(44 citation statements)

References 17 publications

(17 reference statements)

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“…The following compounds have been previously reported and their spectra were consistent with that of the published data: Pivanilides 14 , 15 , 20 , 21 ; 6,10 anilines 16 , 6 28 , 13 aryl bromide 17; 21 and diphenylsilylether 31 . 22 …”

Section: Methodssupporting

confidence: 87%

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

et al. 2011

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Chiral, C2-symmetric imidazolium and imidazolinium ions, as well as the corresponding copper or silver bound carbenoids, have been prepared. Structural study of these compounds by X-ray crystallography reveals a chiral pocket that surrounds the putative carbene site or the metal-carbene bond, at carbon 2, in three of the four ligands prepared. Preliminary investigation into the application of these complexes has shown one of them to be highly enantioselective in the hydrosilylation of acetophenone.

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Section: Methodssupporting

confidence: 87%

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

et al. 2011

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“…[12] Compound 1 also catalysed the benzylation of anilines with styrenes, as shown in Table 4, providing results that compare well with those previously reported which made use of Brønsted acids [14,15] or metal complexes [16,17] as catalysts.…”

Section: Full Papersupporting

confidence: 86%

A Simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ketones

Prades

Corberán

Poyatos

et al. 2009

Chemistry A European J

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One catalyst fits all! One catalyst is active for a wide set of benzylating reactions (see scheme). A tandem process allows the use of aldehydes and ketones as benzylating agents.The compound [IrCp*(OTf)(2)(I(nBu))] (I(nBu)=1,3-di-n-butyl-imidazolylidene) is an effective catalyst in the benzylation of arenes with different benzylating agents, such as alcohols, ethers and styrenes, representing an unprecedented highly versatile catalyst for this type of process. The same compound also catalyses a remarkable tandem process that allows the use of aldehydes and ketones as benzylating agents, through the base-free hydrogenation of C==O bonds with iPrOH and further use of the resulting primary or secondary alcohols as benzylating agents.

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“…In combination with enantioselective separation techniques, such as HPLC, or upon resolution with chiral Brønsted acids this method provides valuable ortho -chiral anilines that could be used as valuable optical active ligands for enantioselective transition-metal catalysis (Scheme 22) [71]. …”

Section: Reviewmentioning

confidence: 99%

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

Rueping¹,

Nachtsheim²

2010

Beilstein J. Org. Chem.

590

353

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SummaryThe development of efficient Friedel–Crafts alkylations of arenes and heteroarenes using only catalytic amounts of a Lewis acid has gained much attention over the last decade. The new catalytic approaches described in this review are favoured over classical Friedel–Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides. Additionally, only low catalyst loadings are needed to provide a wide range of products. Following a short introduction about the origin and classical definition of the Friedel–Crafts reaction, the review will describe the different environmentally benign substrates which can be applied today as an approach towards greener processes. Additionally, the first diastereoselective and enantioselective Friedel–Crafts-type alkylations will be highlighted.

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Acid-Catalyzed ortho-Alkylation of Anilines with Styrenes: An Improved Route to Chiral Anilines with Bulky Substituents

Cited by 62 publications

References 17 publications

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

A Simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ketones

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

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Acid-Catalyzed ortho-Alkylation of Anilines with Styrenes: An Improved Route to Chiral Anilines with Bulky Substituents

Cited by 62 publications

References 17 publications

Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

A Simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ketones

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

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Product

Resources

About

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids

Design and Synthesis of C₂-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids