Manganese-Catalyzed Sustainable Synthesis of Pyrroles from Alcohols and Amino Alcohols

Angewandte Chemie
Fabian KallmeierRhett Kempe

Abstract

The development of reactions that convert alcohols into important chemical compounds saves our fossil carbon resources as alcohols can be obtained from indigestible biomass such as lignocellulose. The conservation of our rare noble metals is of similar importance, and their replacement by abundantly available transition metals, such as Mn, Fe, or Co (base or nonprecious metals), in key technologies such as catalysis is a promising option. Herein, we report on the first base-metal-catalyzed synthesis of pyrroles from alcohols and amino alcohols. The most efficient catalysts are Mn complexes stabilized by PN5 P ligands whereas related Fe and Co complexes are inactive. The reaction proceeds under mild conditions at catalyst loadings as low as 0.5 mol %, and has a broad scope and attractive functional-group tolerance. These findings may inspire others to use Mn catalysts to replace Ir or Ru complexes in challenging dehydrogenation reactions.

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Citations

Jun 20, 2017·Journal of the American Chemical Society·Matthias MastalirKarl Kirchner
Apr 11, 2018·Chemical Communications : Chem Comm·Duo WeiJean-Baptiste Sortais
Jun 5, 2018·Chemistry, an Asian Journal·Manoj Kumar GangwarBasker Sundararaju
Oct 3, 2018·Chemical Communications : Chem Comm·Simone M GillbardHon Wai Lam
Nov 8, 2018·Chemical Communications : Chem Comm·Lalit Mohan KabadwalDebasis Banerjee
Oct 24, 2018·Organic & Biomolecular Chemistry·Vinod G LandgeEkambaram Balaraman
Mar 7, 2020·Organic & Biomolecular Chemistry·Bhaskar PaulSabuj Kundu
Aug 9, 2020·Chemical Communications : Chem Comm·Chunyan ZhangMao-Lin Hu
Aug 7, 2018·Chemical Communications : Chem Comm·Zheng LingWanbin Zhang
May 3, 2018·Nature Communications·Daniel ForbergRhett Kempe
Dec 12, 2018·Chemical Communications : Chem Comm·Antoine Bruneau-VoisineJean-Baptiste Sortais
Nov 18, 2018·ChemCatChem·Oriol Martínez-FerratéWalter Leitner
Mar 28, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jagannath RanaEkambaram Balaraman
Jul 14, 2021·The Journal of Organic Chemistry·Biplab Keshari Pandia, Chidambaram Gunanathan
Aug 10, 2021·Chemical Communications : Chem Comm·Kuhali DasBiplab Maji
Dec 13, 2017·The Journal of Organic Chemistry·Pedro Juan Llabres-CampanerBelén Abarca
Feb 7, 2019·The Journal of Organic Chemistry·Besir KrasniqiWim Dehaen
Nov 27, 2018·The Journal of Organic Chemistry·Khushboo SinghDebasis Banerjee

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