期刊
TETRAHEDRON
卷 73, 期 16, 页码 2225-2233出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.03.001
关键词
Palladacycle; N-alkylation of amines; Cyclometalated palladium
资金
- Department of Science and Technology (DST) [SR/S1/IC-58/2012, SR/S2/RIN-49/2011]
- New Delhi and Department of Atomic Energy (DAE)
Simple pyrazole based palladacycle-phosphine with a high turnover has been developed and applied for the N-alkylation of amines and sulfanilamide using alcohols as substrates by hydrogen borrowing strategy. N-alkylation of primary and secondary amines resulted in high isolated yields at 100-130 degrees C, under solvent free conditions. More challenging secondary aliphatic as well as aromatic alcohols were also successfully utilized as alkylating agents under similar reaction conditions. The turn over number reached up to 43000 for N-benzylation of aniline using benzyl alcohol. Notably, regioselective N-alkylation of 2-aminobenzothiazole and 4-aminobenzenesulfonamide to the corresponding 2-N-(alkylamino) azoles and 4-amino-(N-alkyl)benzenesulfonamides using alcohols as alkylating agents have been achieved using our new pre-catalyst-phosphine system. (C) 2017 Elsevier Ltd. All rights reserved.
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