- Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach
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While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.
- Hatvate, Navnath T.,Takale, Balaram S.,Ghodse, Shrikant M.,Telvekar, Vikas N.
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supporting information
p. 3892 - 3894
(2018/10/02)
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- Formamides as Lewis Base Catalysts in SNReactions—Efficient Transformation of Alcohols into Chlorides, Amines, and Ethers
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A simple formamide catalyst facilitates the efficient transformation of alcohols into alkyl chlorides with benzoyl chloride as the sole reagent. These nucleophilic substitutions proceed through iminium-activated alcohols as intermediates. The novel method, which can be even performed under solvent-free conditions, is distinguished by an excellent functional group tolerance, scalability (>100 g) and waste-balance (E-factor down to 2). Chiral substrates are converted with excellent levels of stereochemical inversion (99 %→≥95 % ee). In a practical one-pot procedure, the primary formed chlorides can be further transformed into amines, azides, ethers, sulfides, and nitriles. The value of the method was demonstrated in straightforward syntheses of the drugs rac-Clopidogrel and S-Fendiline.
- Huy, Peter H.,Motsch, Sebastian,Kappler, Sarah M.
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supporting information
p. 10145 - 10149
(2016/08/16)
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- Microwave induced halodecarboxylation of α,β-unsaturated carboxylic acids
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Halodecarboxylations of α,β-unsaturated carboxylic acids 1a-g, 4 by N-cholorobenzotriazole under 5-10 minutes of microwave irradiation gave the corresponding β-arylvinyl halides 3a-g, 5 in yields of 70-90%.
- Katritzky, Alan R.,Majumder, Suman,Jain, Ritu
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p. 1073 - 1075
(2007/10/03)
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