Green oxidative synthesis of primary amides from primary alcohols or aldehydes catalyzed by a cryptomelane-type manganese oxide-based octahedral molecular sieve, OMS-2

Kazuya Yamaguchi, Hiroaki Kobayashi, Ye Wang, Takamichi Oishi, Yoshiyuki Ogasawara, Noritaka Mizuno

研究成果: Article

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In this study, a new green synthetic route to primary amides, that is, aerobic oxidative amidation of primary alcohols or aldehydes with ammonia, has been developed. In the presence of a cryptomelane-type manganese oxide-based octahedral molecular sieve (OMS-2), various kinds of structurally diverse primary alcohols or aldehydes including aromatic, olefinic, heteroaromatic, and aliphatic ones can be converted into the corresponding primary amides in moderate to high yields (20 examples from primary alcohols and 11 examples from aldehydes). Furthermore, gram-scale amidation is also effective, and the analytically pure primary amides can easily be isolated. The present catalysis by OMS-2 is truly heterogeneous in nature, and the retrieved OMS-2 catalyst can be reused several times (at least 12 times for the amidation of 2-pyridinemethanol). Though the formation rates of the corresponding primary amide are gradually decreased by repeating reuse experiments, OMS-2 can be regenerated by calcination. The present OMS-2-catalyzed amidation of primary alcohols is composed of four relay steps: (i) oxidative dehydrogenation of primary alcohols, (ii) dehydrative condensation of aldehydes with ammonia, (iii) oxidative dehydrogenation of aldimines, and (iv) hydration of nitriles to form the corresponding primary amides. All steps (i)-(iv) can be promoted by the presence of OMS-2.

元の言語English
ページ(範囲)318-327
ページ数10
ジャーナルCatalysis Science and Technology
3
発行部数2
DOI
出版物ステータスPublished - 2013 2

ASJC Scopus subject areas

  • Catalysis

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