Convenient Unsymmetrical Disulfane Synthesis: Basic Zeolite-Catalyzed Thiol-Disulfane Exchange Reaction

Eiji Yamamoto, Yasutaka Kawai, Kei Takakura, Moemi Kimura, Haruno Murayama, Hironobu Matsueda, Shujiro Otsuki, Hiroshi Sakata, Makoto Tokunaga

研究成果: ジャーナルへの寄稿学術誌査読

1 被引用数 (Scopus)

抄録

Convenient catalytic synthetic methods for the preparation of unsymmetrical disulfanes are described. Na-exchanged X type zeolite (Na-X), commercially available as MS-13X, effectively catalyzes thiol-disulfane exchange reactions with 1.0 equivalent of thiols and 2.5–3.0 equivalents of disulfanes at 10 °C to room temperature under air. The reactions of sterically-hindered disulfanes or electron-deficient thiol substrates require high temperatures under inert atmospheres to maintain the good product yields. Various functionalized thiols and disulfanes are tolerant in the present catalytic systems, affording the corresponding unsymmetrical disulfanes in good-to-high yields (up to 96 %). The Na-X catalyst was successfully recycled 10 times without loss of yield. Preliminary mechanistic studies suggest the involvement of base-catalyzed SN2-S displacement and/or addition-elimination mechanisms, assisted by hydrogen-bonding interactions.

本文言語英語
ページ(範囲)4694-4699
ページ数6
ジャーナルChemCatChem
13
22
DOI
出版ステータス出版済み - 11月 22 2021

!!!All Science Journal Classification (ASJC) codes

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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