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Synlett 2021; 32(02): 219-223
DOI: 10.1055/s-0040-1706538
letter

Reductive Ring-Opening 1,3-Difunctionalizations of Arylcyclopropanes with Sodium Metal

Shuo Wang
,
Atsushi Kaga
,
Hideki Yorimitsu  ∗
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
› Author AffiliationsThis work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, JP19H00895), the Core Research for Evolutional Science and Technology (JST CREST, JPMJCR19R4), and by the Asahi Glass Foundation. We thank KOBELCO ECO-Solutions Co., Ltd. for providing sodium dispersion.
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Abstract

Sodium dispersion promotes reductive ring opening of arylcyclopropanes. The presence of a reduction-resistant electrophile, such as methoxypinacolatoborane, epoxide, oxetane, paraformaldehyde, or chlorotrimethylsilane, during the reductive ring opening event leads to the formation of 1,3-difunctionalized 1-arylalkanes by immediate trappings of the resulting two reactive carbanions. In particular, the ring-opening 1,3-diborylations of arylcyclopropanes afford 1,3-diborylalkanes with high syn selectivity.

Key words

carbanions - cleavage - diastereoselectivity - electron transfer - metalation - reduction - ring opening - sodium

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706538.
  • Supporting Information


Publication History

Received: 27 August 2020

Accepted after revision: 16 September 2020

Article published online:
22 October 2020

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