Friedel-Crafts cyclialkylations of certain mono- and diphenyl-substituted alcohols and alkyl chlorides

Khalaf, A. A.; Roberts, Royston M.

doi:10.1021/jo00799a001

Cited by 37 publications

(9 citation statements)

References 3 publications

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“…The structure of the title compound was first determined by Ehrenberg (1966) using film data and more recently Choi & Marinkas (1980) redetermined the structure at room tempera- BI(9,10-DIHYDRO-9,10-ANTHRACENEDIYL) some of the reactions that had been studied previously [Roberts, Anderson, Khalaf & Low (1971); Roberts, Bantel & Low (1973); Khalaf & Roberts (1972); ; Roberts & AbdelBaset (1976)]. …”

Section: Bis[(13-dithian-2-ylidene) Methyl]aminementioning

confidence: 99%

Redetermination of the structure of bi(9,10-dihydro-9,10-anthracenediyl) at 198 K

Abboud¹,

Simonsen²,

Roberts³

1990

Acta Crystallogr C

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Section: Bis[(13-dithian-2-ylidene) Methyl]aminementioning

confidence: 99%

Redetermination of the structure of bi(9,10-dihydro-9,10-anthracenediyl) at 198 K

Abboud¹,

Simonsen²,

Roberts³

1990

Acta Crystallogr C

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“…In this context, direct substitution of the hydroxy group in alcohols by nucleophiles could be considered as an ideal process because of the wide availability of the starting materials and the generation of H 2 O as the only side product. However, the main limitation of this strategy is that an excess of sulfuric acid, polyphosphoric acid, [1] or a stoichiometric amount of a Lewis acid [2] is required, and so the range of possible nucleophiles is limited. Therefore, the development of catalytic versions of this reaction remains as a major objective of the modern organic chemistry (Scheme 1).…”

mentioning

confidence: 99%

Brønsted Acid‐Catalyzed Nucleophilic Substitution of Alcohols

et al. 2006

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Abstract:Simple Brønsted acids such as p-toluenesulfonic acid monohydrate (PTS) or polymer-bound p-toluenesulfonic acid efficiently catalyze the direct nucleophilic substitution of the hydroxy group of allylic and benzylic alcohols with a large variety of carbon-and heteroatom-centered nucleophiles. Reaction conditions are mild, the process is conducted under an atmosphere of air without the need for dried solvents, and water is the only side product of the reaction.Keywords: alcohols; C À C coupling; nucleophilic substitution; supported catalysts; synthetic methodsThe construction of C À C bonds is a fundamental reaction in organic synthesis and coupling reactions between reactive nucleophiles (NuH) and halides (RX) or related species are one of the most used strategies. In this context, direct substitution of the hydroxy group in alcohols by nucleophiles could be considered as an ideal process because of the wide availability of the starting materials and the generation of H 2 O as the only side product. However, the main limitation of this strategy is that an excess of sulfuric acid, polyphosphoric acid, [1] or a stoichiometric amount of a Lewis acid [2] is required, and so the range of possible nucleophiles is limited. Therefore, the development of catalytic versions of this reaction remains as a major objective of the modern organic chemistry (Scheme 1). Recent advances in this field are based on the use of transition metal complexes as catalysts. Remarkable are the Ru-, [3] Re-, [4] and Au-catalyzed [5] propargylation of nucleophiles with propargylic alcohols, the Tsuji-Trost reaction of allylic alcohols with active methylene compounds, [6] the reaction of secondary benzylic alcohols with different nucleophiles catalyzed by La, Sc, or Hf salts, [7] and the Fe-, or Au-catalyzed arylation of benzylic alcohols.[8] In addition, InCl 3 has emerged as a powerful catalyst to perform direct nucleophilic substitution of allylic and benzylic alcohols. [9] Although the catalytic activation of alcohols is thought to be difficult due to the poor leaving ability of the OH group, we have recently found that simple Brønsted acids like p-toluenesulfonic acid monohydrate (PTS) catalyze the direct nucleophilic substitution of propargylic alcohols.[10] Herein we report a strategy involving simple Brønsted acid-catalyzed activation of allylic and benzylic alcohols as a method for the direct formation of new C À C and C À heteroatom bonds from carbon (active methylene compounds, aromatic and heteroaromatic compounds), nitrogen, sulfur, and oxygen nucleophiles and alcohols. Surprisingly, the Brønsted acid-catalyzed direct substitution of allylic alcohols has not been reported in the literature and so no systematic study has so far been performed. Moreover, in some recent papers this reaction has been reported not to proceed at all. [9b] Despite all these negative forewarnings, we decided to investigate the reaction of allylic alcohol 1a as a model substrate with selected nucleophiles 2-8 under PTS-catalyzed conditions (Sche...

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“…Many reagents and methodologies are developed for Fridel-Crafts alkylation reactions. [2][3][4][5][6][7] The new environmental legislation pushes for the replacement of all liquid acids by solid acid catalysts which are environmentally more friendly catalysts and which lead to minimal pollution and waste. 8 Also, in the recent years, the use of reagents and catalysts on solid supports has received significant attention.…”

Section: Scheme 1 Reaction Of Aromatics With Benzyl or Tert-butyl Chmentioning

confidence: 99%

Silica Chloride Mediated Alkylation of Electron-rich Aromatics by Benzyl or tert-Butyl Chloride

Mohanazadeh¹,

Amini²

2010

Bulletin of the Korean Chemical Society

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Friedel-Crafts cyclialkylations of certain mono- and diphenyl-substituted alcohols and alkyl chlorides

Cited by 37 publications

References 3 publications

Redetermination of the structure of bi(9,10-dihydro-9,10-anthracenediyl) at 198 K

Redetermination of the structure of bi(9,10-dihydro-9,10-anthracenediyl) at 198 K

Brønsted Acid‐Catalyzed Nucleophilic Substitution of Alcohols

Silica Chloride Mediated Alkylation of Electron-rich Aromatics by Benzyl or tert-Butyl Chloride

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