130728-22-2Relevant academic research and scientific papers
Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile
Tsuji, Hiroaki,Hashimoto, Keisuke,Kawatsura, Motoi
, p. 8837 - 8841 (2019)
The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.
Concurrent stepwise and concerted substitution reactions of 4-methoxybenzyl derivatives and the lifetime of the 4-methoxybenzyl carbocation
Amyes, Tina L.,Richard, John P.
, p. 9507 - 9512 (2007/10/02)
The rates of reaction of 4-methoxybenzyl chloride, pentafluorobenzoate, and 3,5-dinitrobenzoate in 50:50 (v/v) trifluoroethanol/water are zero order in the concentration of azide ion. These reactions give good yields of the azide adduct from trapping of t
