2016
DOI: 10.1002/chem.201603057
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Mechanochemical Strecker Reaction: Access to α‐Aminonitriles and Tetrahydroisoquinolines under Ball‐Milling Conditions

Abstract: A mechanochemical version of the Strecker reaction for the synthesis of α-aminonitriles was developed. The milling of aldehydes, amines, and potassium cyanide in the presence of SiO2 gave the corresponding α-aminonitriles in good to high yields. The high efficiency of the mechanochemical Strecker-type multicomponent reaction allowed the one-pot synthesis of tetrahydroisoquinolines after a subsequent internal N-alkylation reaction.

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Cited by 68 publications
(51 citation statements)
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“…An umber of multi-component reactions have been adapted to mechanochemistry,including Biginelli, [105] Strecker, [106] Ugi and Passerini reactions, [67] validating orthogonal and cascade reaction designs in as olvent-free environment. Thep otential of mechanochemistry in that sense was ex-plored by Hernµndez et al [107] who developed ao ne-step 5component route to build Re I complexes from asimple metal carbonyl, based on orthogonal oxidative addition and ligand exchange (Figure 11 a).…”
Section: Multi-component and Multi-step Reactionsmentioning
confidence: 99%
“…An umber of multi-component reactions have been adapted to mechanochemistry,including Biginelli, [105] Strecker, [106] Ugi and Passerini reactions, [67] validating orthogonal and cascade reaction designs in as olvent-free environment. Thep otential of mechanochemistry in that sense was ex-plored by Hernµndez et al [107] who developed ao ne-step 5component route to build Re I complexes from asimple metal carbonyl, based on orthogonal oxidative addition and ligand exchange (Figure 11 a).…”
Section: Multi-component and Multi-step Reactionsmentioning
confidence: 99%
“…Before mechanochemistry was established for advanced materials syntheses, ball milling was primarily used for particle‐size reduction and alloying . Recent studies in the fields of pharmaceutical chemistry, organic chemistry, and inorganic chemistry, especially in the field of metal–organic frameworks (MOFs), have demonstrated the tremendous potential of mechanochemistry. However, the mechanochemical synthesis of porous carbon has remained largely unexplored.…”
Section: Introductionmentioning
confidence: 99%
“…Multicomponent reactions (MCRs) have gained importance because of their efficiency and effectiveness as a method for one-pot synthesis of a wide range of heterocycles [1][2][3][4][5][6]. The optimal MCR is sufficiently flexible.…”
Section: Introductionmentioning
confidence: 99%