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Cobalt‐Catalyzed Alkylation of Secondary Alcohols with Primary Alcohols via Borrowing Hydrogen/Hydrogen Autotransfer
Author(s) -
Freitag Frederik,
Irrgang Torsten,
Kempe Rhett
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701211
Subject(s) - catalysis , cobalt , chemistry , primary (astronomy) , alkylation , base metal , combinatorial chemistry , hydrogen , ligand (biochemistry) , pincer movement , organic chemistry , substrate (aquarium) , materials science , oceanography , geology , biochemistry , physics , receptor , astronomy , welding , metallurgy
Alcohols are promising sustainable starting materials because they can be obtained from abundant and indigestible biomass. The substitution of expensive noble metals in catalysis by earth abundant 3d metals, such as Mn, Fe, or Co, (nonprecious or base metals) is a related key concept with respect to sustainability. Here, we report on the first cobalt‐catalyzed alkylation of secondary alcohols with primary alcohols. Easy‐to‐synthesize and easy‐to‐activate PN 5 P‐pincer‐ligand‐stabilized Co complexes developed in our laboratory mediate the reaction most efficiently. The catalysis is applicable to a broad substrate scope and proceeds under relatively mild conditions. We have even demonstrated the coupling of a variety of purely aliphatic alcohols with a base or nonprecious metal catalyst. Mechanistic studies indicate that the reaction follows the borrowing hydrogen or hydrogen autotransfer concept.