Ligand‐promoted dehydrogenative coupling of γ‐/β‐amino alcohols with ketones to N‐heterocycles via molybdenum catalysts

Author:

Wang Yuanyuan1,Ma Ning12,Yan Xiuli3,Li Libin24,Lin Qing1,Han Peng1,Zhao Bin1,Mahmood Qaiser5ORCID,Liu Qingbin2,Wang Zheng12ORCID

Affiliation:

1. College of Science Hebei Agricultural University Baoding China

2. Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Material Science Institution Hebei Normal University Shijiazhuang China

3. College of Material Science and Engineering Hebei University of Engineering Handan China

4. Shijiazhuang Chiral Chemical Co., Ltd Shijiazhuang China

5. Chemistry and Chemical Engineering Guangdong Laboratory Shantou China

Abstract

Molybdenum‐based efficient and broadly applicable catalytic system is presented for the dehydrogenative coupling of γ‐/β‐amino alcohols with ketones. In particular, complex Mo(CO)6 in combination with Xantphos and t‐BuOK as base provides direct synthesis of structurally diverse quinoline, pyridine, and pyrrole compounds (total 55 examples) with isolated yields up to 92%. Low catalyst loading, cost‐effective, and high catalytic activities with high tolerance to stand with diverse functional groups are additional features of these molybdenum catalysts exhibiting high efficacy to replace the precious metal catalysts such as ruthenium and iridium. Furthermore, the DFT and experimental studies were explored for the reaction mechanism which can assist in broadening the scope of the molybdenum catalysts for different transformation reactions.

Publisher

Wiley

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