Cyclometalated palladium pre-catalyst for N-alkylation of amines using alcohols and regioselective alkylation of sulfanilamide using aryl alcohols

被引：32

作者：

Mamidala, Ramesh ^{[1
]}

Mukundam, Vanga ^{[1
]}

Dhanunjayarao, Kunchala ^{[1
]}

Venkatasubbaiah, Krishnan ^{[1
]}

机构：

[1] HBNI, Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Orissa, India

来源：

TETRAHEDRON | 2017年 / 73卷 / 16期

关键词：

Palladacycle; N-alkylation of amines; Cyclometalated palladium; BORROWING HYDROGEN; HETEROCYCLIC CARBENE; SELECTIVE ALKYLATION; IRIDIUM COMPLEX; EFFICIENT; PALLADACYCLES; ARYLATION; ANILINES; HECK;

D O I：

10.1016/j.tet.2017.03.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2225 / 2233

页数：9

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