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Direct synthesis of ring-fused quinolines and pyridines catalyzed by NNHY-ligated manganese complexes (Y = NR2 or SR)

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journal contribution
posted on 2021-12-23, 11:42 authored by Zheng Wang, Qing Lin, Ning Ma, Song Liu, Mingyang Han, Xiuli Yan, Qingbin Liu, Gregory A Solan, Wen-Hua Sun
Four cationic manganese(I) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1–Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (where NNH is a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alcohol with a ketone or secondary alcohol; NNHS-ligated Mn-4 proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5–5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and experimental evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclic N-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.

History

Citation

Catal. Sci. Technol., 2021,11, 8026-8036

Author affiliation

School of Chemistry

Version

  • AM (Accepted Manuscript)

Published in

Catalysis Science & Technology

Volume

11

Pagination

8026-8036

Publisher

Royal Society of Chemistry (RSC)

issn

2044-4753

eissn

2044-4761

Acceptance date

2021-11-05

Copyright date

2021

Available date

2022-11-09

Language

English