Direct Synthesis of Symmetrical Azines from Alcohols and Hydrazine Catalyzed by a Ruthenium Pincer Complex: Effect of Hydrogen Bonding | Zendy

Jonathan O. Bauer | Zendy; Gregory Leitus | Zendy; Yehoshoa BenDavid | Zendy; David Milstein | Zendy

Open Access

Direct Synthesis of Symmetrical Azines from Alcohols and Hydrazine Catalyzed by a Ruthenium Pincer Complex: Effect of Hydrogen Bonding

Author(s) -

Jonathan O. Bauer,

Gregory Leitus,

Yehoshoa BenDavid,

David Milstein

Publication year - 2016

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.6b02946

Subject(s) - ruthenium , pincer movement , chemistry , hydrazine (antidepressant) , catalysis , hydrate , hydrogen bond , supramolecular chemistry , combinatorial chemistry , organic chemistry , coupling reaction , medicinal chemistry , photochemistry , polymer chemistry , crystal structure , molecule , chromatography

Azines (2,3-diazabuta-1,3-dienes) are a widely used class of compounds with conjugated C=N double bonds. Herein, we present a direct synthesis of azines from alcohols and hydrazine hydrate. The reaction, catalyzed by a ruthenium pincer complex, evolves dihydrogen and can be run in a base-free version. The dehydrogenative coupling of benzylic and aliphatic alcohols led to good conversions and yields. Spectroscopic evidence for a hydrazine-coordinated dearomatized ruthenium pincer complex was obtained. Isolation of a supramolecular crystalline compound provided evidence for the important role of hydrogen bonding networks under the reaction conditions.

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