- Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
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An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary ami
- Chang, Junbiao,Du, Yangxu,Hao, Wei,Hou, Jiao,Lu, Qing,Yu, Wenquan
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p. 16223 - 16226
(2021/09/22)
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- Facile Direct Coupling Reactions of MOM-protected Benzylic Alcohols Using Aluminum Chloride
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MOM group is one of the most commonly used protecting groups for alcohols. This study describes novel direct functionalization of the MOM-protected benzylic alcohols. Preparation of allylic compounds from benzyl MOM ethers was successfully achieved by utilization of allyltrimethylsilane and AlCl3. In addition, direct azidation of benzyl MOM ethers using TMSN3 was successful carried out under AlCl3-mediated reaction conditions. These results demonstrate that this novel synthetic procedure is a promising approach to direct functionalization of MOM-protected alcohols including allylation and azidation.
- Bui, Tien Tan,Kim, Hee-Kwon
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supporting information
p. 1195 - 1198
(2021/08/03)
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- Direct AlCl3-catalyzed transformation of benzyl THP ethers and allyl benzyl ethers
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THP and allyl groups are frequently used for the protection of alcohols. In this study, novel direct transformations of benzyl THP ethers and allyl benzyl ethers, protected forms of alcohols, are reported. TMSN3 and AlCl3 were employ
- Bui, Tien Tan,Kim, Hee-Kwon
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p. 388 - 397
(2020/10/15)
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- Iron-catalysed 1,2-aryl migration of tertiary azides
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1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.
- Wei, Kaijie,Yang, Tonghao,Chen, Qing,Liang, Siyu,Yu, Wei
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supporting information
p. 11685 - 11688
(2020/10/19)
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- A Direct Br?nsted Acid-Catalyzed Azidation of Benzhydrols and Carbohydrates
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Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Br?nsted acid HBF4·OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron-donating and electron-withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well-tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.
- Regier, Jeffery,Maillet, Robert,Bolshan, Yuri
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p. 2390 - 2396
(2019/04/14)
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- Fe(OTf)3-catalyzed reaction of benzylic acetates with organosilicon compounds
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Fe(OTf)3-catalyzed reaction of benzylic acetates with allyltrimethylsilane, azidotrimethylsilane, and cyanotrimethylsilane afforded the corresponding allylated, azido, and cyano products in high yields. 2-Trimethylsilyl-substituted benzofuran and indole worked well to furnish the benzyl-substituted benzofuran and indoles. Georg Thieme Verlag Stuttgart New York.
- Chan, Li Yan,Kim, Sundae,Chung, Wan Ting,Long, Chong,Kim, Sunggak
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experimental part
p. 415 - 419
(2011/04/22)
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- Syntheses and reactions of 1-amino-2,2-dialkylcyclopropane-1- carbonitriles and -carboxamides - Potential precursors of ACC derivatives
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The direct cyclization of 2-amino-4-chloro,3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2- dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(tert-butylamino)-2-benzyl-2-methylcyclopropane- carbonitriles and the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskil-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.
- Aelterman, Wim,Tehrani, Kourosch Abbaspour,Coppens, Wim,Huybrechts, Tom,De Kimpe, Norbert,Tourwe, Dirk,Declercq, Jean-Paul
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p. 239 - 250
(2007/10/03)
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- Conversion of alkenes and alcohols to azides over zeolite-supported sodium azide
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Zeolite-supported sodium azide reagents are versatile catalysts for the conversion of various alkenes and alcohols to the corresponding azides in good yield under mild conditions.
- Sreekumar,Padmakumar,Rugmini
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p. 1133 - 1134
(2007/10/03)
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- Nucleophilic Substitution Reactions of Alkyl Halides By Using New Polymer-Supported Reagents Containing Hemin
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A new polymer reagent consisting of hemin, divinylbenzene, and 2-methyl-5-vinylpyridine was synthesized by suspension copolymerization.Substitution reactions of primary, secondary, and tertiary alkyl halides with the hemin copolymer combined with cyanide, azide, and thiocyanate ions were given satisfactory yields.This reaction mechanism was revealed to be a SNi type on the basis of stereochemical study.The hemin copolymer was not only a polymer-supported reagent with functional capabilities, but also served to separate the product from the reaction mixture.
- Saito, Kiyoshi,Harada, Kaoru
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p. 2562 - 2566
(2007/10/02)
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- IMINOPHOSPHORANE-MEDIATED TRANSFORMATION OF TERTIARY ALCOHOLS INTO t-ALKYLAMINES AND THEIR N-PHOSPHORYLATED DERIVATIVES
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Novel azidation of tertiary alcohols by means of trimetylsilyl azide in the presence of boron trifluoride etherate has been worked out.The Staudinger reaction of crude azides with triethyl phosphite affords the corresponding iminophosphoranes which can be directly transformed into diethyl N-(t-alkyl)phosphoroamidates or t-alkylamine tosylates.
- Koziara, Anna,Zwierzak, Andrzej
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p. 6513 - 6516
(2007/10/02)
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- Lewis Acid Catalyzed Conversion of Alkenes and Alcohols to Azides
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Hydrazoic acid, though unreactive to alkenes, adds readily to enol ethers.In the presence of Lewis acids, in particular TiCl4, addition takes place readily to phenylethylenes or 1,1-disubstituted ethylenes to produce alkyl azides.Regiochemical, electronic, and steric influences were explored.TiCl4 also served to catalyze conversion of benzyl or tertiary alcohols to azides.Monosubstituted alkenes or primary alcohols are not affected.
- Hassner, Alfred,Fibiger, Richard,Andisik, Donald
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p. 4237 - 4244
(2007/10/02)
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