Efficient Simmons–Smith cyclopropanation with Zn/Cu and CH 2 I 2 | Zendy

Fujii Kanami | Zendy; Shiine Kodai | Zendy; Misaki Tomonori | Zendy; Sugimura Takashi | Zendy

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Efficient Simmons–Smith cyclopropanation with Zn/Cu and CH 2 I 2

Author(s) -

Fujii Kanami,

Shiine Kodai,

Misaki Tomonori,

Sugimura Takashi

Publication year - 2013

Publication title -

applied organometallic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.53

H-Index - 71

eISSN - 1099-0739

pISSN - 0268-2605

DOI - 10.1002/aoc.2935

Subject(s) - chemistry , solvent , boiling point , cyclopropanation , medicinal chemistry , ether , organic chemistry , catalysis

An appropriate solvent to perform the original Simmons–Smith reaction was reinvestigated. Among available solvents, cyclopentyl methyl ether (CPME), a recently commercialized ethereal solvent, was found to be the best so far. Compared with Et 2 O under reflux – the commonest conditions – reaction completion in CPME at 50 °C was about 10 times faster. The product yields and selectivities were mostly identical to those with Et 2 O, but were better in some cases; e.g. 13–56% with 2‐cyclohexenol. The good performance of CPME should be mainly due to its moderate polarity and high boiling point. Copyright © 2012 John Wiley & Sons, Ltd.

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