Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization

doi:10.6023/cjoc201908017

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 53-60.DOI: 10.6023/cjoc201908017 Previous Articles Next Articles

NN型双齿半夹心Ru(II)化合物:无受体脱氢环化合成喹啉和吡咯衍生物的催化剂

胡博文, 张宇哲, 尹鸽平, 陈大发

哈尔滨工业大学化工与化学学院哈尔滨 150001

收稿日期:2019-08-11 修回日期:2019-09-16 发布日期:2019-09-25
通讯作者: 胡博文 E-mail:bowenhu@hit.edu.cn
基金资助:
国家自然科学基金（Nos.21672045，21871068）、中国博士后基金（No.2016M591519）、黑龙江省博士后基金（No.LBH-Z16069）及黑龙江省自然科学基金（Nos.B2018005，LC2018005）资助项目.

Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization

Hu Bowen, Zhang Yuzhe, Yin Geping, Chen Dafa

School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001

Received:2019-08-11 Revised:2019-09-16 Published:2019-09-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21672045, 21871068), the China Postdoctoral Science Foundation (No. 2016M591519), the Heilongjiang Provincial Postdoctoral Foundation (No. LBH-Z16069), and the National Natural Science Foundation of Heilongjiang Province (Nos. B2018005, LC2018005).

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Abstract

Four (h⁶-p-cymene)Ru(II) complexes with bidentate NN ligands, (h⁶-p-cymene)Ru(C₅H₄N-C₅H₃N-OH) (1), (h⁶-p-cymene)Ru(C₅H₄N-CH₂-C₅H₄N) (2), (h⁶-p-cymene)Ru(C₅H₄N-CH₂-C₅H₃N-OH) (3) and (h⁶-p-cymene)Ru(C₅H₄N-CH₂-C₅H₃N-OCH₃) (4) were prepared. These complexes were all characterized by¹H NMR, ¹³C NMR and elemental analysis, and complex 2 was further determined by single crystal crystallography. Complexes 1~4 were treated as catalysts for cyclizations of amino alcohols with ketones, and complex 3 exhibited the highest activity. The cyclization reactions proceeded in toluene with 0.5 mol% catalyst loading, and a series of quinolines and pyrroles were synthesized.

Key words: half-sandwich, ruthenium, acceptorless dehydrogenative cyclization, bidentate ligand, 2-hydroxypyridine

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Hu Bowen, Zhang Yuzhe, Yin Geping, Chen Dafa. Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 53-60.

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NN型双齿半夹心Ru(II)化合物:无受体脱氢环化合成喹啉和吡咯衍生物的催化剂

Half-Sandwich Ruthenium(II) Complexes with Bidentate NN Ligands:Active Catalysts for the Synthesis of Quinolines and Pyrroles by Acceptorless Dehydrogenative Cyclization

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