A Facile and Green Protocol for Nucleophilic Substitution Reactions of Sulfonate Esters by Recyclable Ionic Liquids [bmim][X]

Yajun Liu; Yongnan Xu; Sun Ho Jung; Junghyun Chae

doi:10.1055/s-0032-1317473

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(18): 2692-2698
DOI: 10.1055/s-0032-1317473

letter

A Facile and Green Protocol for Nucleophilic Substitution Reactions of Sulfonate Esters by Recyclable Ionic Liquids [bmim][X]

Autor*innen

Yajun Liu

^aKey Laboratory of Structure-Based Drugs Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China

^bDepartment of Chemistry and Research Institute of Basic Sciences, Sungshin Women’s University, Seoul, 136-742, Korea Fax: +82(2)9202058 eMail: jchae@sungshin.ac.kr
Yongnan Xu

^aKey Laboratory of Structure-Based Drugs Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. of China
Sun Ho Jung

^bDepartment of Chemistry and Research Institute of Basic Sciences, Sungshin Women’s University, Seoul, 136-742, Korea Fax: +82(2)9202058 eMail: jchae@sungshin.ac.kr
Junghyun Chae*

^bDepartment of Chemistry and Research Institute of Basic Sciences, Sungshin Women’s University, Seoul, 136-742, Korea Fax: +82(2)9202058 eMail: jchae@sungshin.ac.kr

Abstract

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Abstract

Ionic liquids [bmim][X] (X = Cl, Br, I, OAc, SCN) are highly efficient reagents for nucleophilic substitution reactions of sulfonate esters derived from primary and secondary alcohols. The counter anions (X^–) of the ionic liquids, [bmim][X], effectively replace the sufonates affording the corresponding substitution products such as alkyl halides, acetates, and thiocyanides in excellent yields. The newly developed protocol is very environmentally attractive because the reactions use stoichiometric amounts of ionic liquids as sole reagents in most cases and do not require additional solvents, any other activating reagents, non-conventional equipment, or special precautions. Moreover, these ionic liquids can be readily recycled without loss of reactivity, making the whole process ‘greener’.

Key words

ionic liquids - nucleophilic substitution - halogenation - recyclability - green chemistry

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Referenzen

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18 Since no elimination by-product was detected, the low yield of entry 12 was attributed to substrate instability.
19 The products in Table 3, except those in entry 14, did not need further purification. The products from entry 14 were purified by column chromatography (see the Supporting Information).
20 Sodium halides were previously reported for a similar reaction, but details on the reaction conversions or yields were not provided. See ref. 15b.

Zusatzmaterial

Supporting Information (PDF) (opens in new window)