Acid-catalyzed ortho-alkylation of anilines with styrenes:: An improved route to chiral anilines with bulky substituents

被引：58

作者：

Cherian, AE ^{[1
]}

Domski, GJ ^{[1
]}

Rose, JM ^{[1
]}

Lobkovsky, EB ^{[1
]}

Coates, GW ^{[1
]}

机构：

[1] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 23期

关键词：

D O I：

10.1021/ol051916j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of para-substituted anilines with styrene derivatives at elevated temperatures, when catalyzed by CF3SO3H, results in highly chemoselective ortho-alkylation of the aniline. When R = H, dialkylation can be achieved by varying the ratio of styrene to aniline. Several different substituted anilines and styrenes were examined, and good yields (42-87%) were obtained, except in the case where electron-withdrawing substituents are present on the styrene.

引用

页码：5135 / 5137

页数：3

共 21 条

[11] MECHANISM OF REARRANGEMENT OF N-ALKYLANILINES [J].

HART, H ;

KOSAK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :116-&

[12]

Herrmann W. A., 2002, APPL HOMOGENEOUS CAT

[13]

March J., 1992, Advanced Organic Chemistry: Reactions, Mechanism, and Structures, V4th, P536

[14] Addition polymerization of cyclopentene with nickel and palladium catalysts [J].

McLain, SJ ;

Feldman, J ;

McCord, EF ;

Gardner, KH ;

Teasley, MF ;

Coughlin, EB ;

Sweetman, BJ ;

Johnson, LK ;

Brookhart, M .

MACROMOLECULES, 1998, 31 (19) :6705-6707

[15] Stereoselective alternating copolymerization of carbon monoxide with alkenes [J].

Nozaki, K ;

Hiyama, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :248-253

[16]

OLIFIROV DI, 1992, ZH ORG KHIM+, V28, P1206

[17]

Parshall G.W. Ittel., 1992, HOMOGENEOUS CATALYSI, V2nd edn

[18] Syndiotactic-specific polymerization of propene with nickel-based catalysts .2. Regiochemistry and stereochemistry of the initiation steps [J].

Pellecchia, C ;

Zambelli, A ;

Oliva, L ;

Pappalardo, D .

MACROMOLECULES, 1996, 29 (22) :6990-6993

[19] Polymerization of propylene by a new generation of iron catalysts: Mechanisms of chain initiation, propagation, and termination [J].

Small, BL ;

Brookhart, M .

MACROMOLECULES, 1999, 32 (07) :2120-2130

[20] N-H activation vs. C-H activation:: ruthenium-catalysed regioselective hydroamination of alkynes and hydroarylation of an alkene with N-methylaniline [J].

Uchimaru, Y .

CHEMICAL COMMUNICATIONS, 1999, (12) :1133-1134

← 1 2 3 →