A Ruthenium‐Based Catalytic System for a Mild Borrowing‐Hydrogen Process. Issue 8 (30th January 2015)

• Record Type: Journal Article
• Authors: Jumde, Varsha R.; Gonsalvi, Luca; Guerriero, Antonella; Peruzzini, Maurizio; Taddei, Maurizio
• Is Part Of: European journal of organic chemistry. Issue 8(2015)
• Page Start: 1829
• Page End: 1833
• Publication Date: 2015-01-30
• Subjects: Homogeneous catalysis -- Hydrogen transfer -- Alkylation -- Ruthenium -- Amines -- Alcohols; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403636
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The alkylation of arylamines using stoichiometric amounts of aliphatic and benzylic alcohols in the presence of t BuOK was carried out at 55 °C using a low catalyst loading of [Ru(cod)Cl2 ] n /PTA (1, 3, 5‐triaza‐7‐phosphaadamantane). The overall borrowing‐hydrogen process does not require a controlled nitrogen atmosphere, and it could also be carried out at room temperature using higher loading of base. A wide range of substrates can be used in this transformation, and it has a good tolerance of different substituents. This catalytic system proved also to be efficient for other hydrogen‐transfer reactions such as a tandem oxidation/C–C coupling between 1‐phenylethanol and primary alcohols. Abstract : The alkylation of anilines with alcohols is possible at 55 °C using a Ru catalyst (2.5 mol‐%) and a ligand that does not require an inert atmosphere.