Proton-catalyzed hydroamination and hydroarylation reactions of anilines and alkenes: A dramatic effect of counteranions on reaction efficiency

被引:238
作者
Anderson, LL [1 ]
Arnold, J [1 ]
Bergman, RG [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja053700i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The anilinium salt, [PhNH3][B(C6F5)4], has been identified as a catalyst for the hydroamination and hydroarylation of several different types of alkenes with anilines. The weakly coordinating counterion of this acid plays a key role in this transformation. The reaction is facile for styrenes and tolerates norbornene, cyclic alkenes, and cyclohexadiene. Selectivity between hydroamination and hydroarylation products can be tuned using reaction time, temperature, and substrate substitution. Details regarding the substrate scope and selectivity of this hydroamination/hydroarylation reaction are discussed. Copyright © 2005 American Chemical Society.
引用
收藏
页码:14542 / 14543
页数:2
相关论文
共 17 条
[1]   TiCl4-catalyzed intermolecular hydroamination reactions of norbornene [J].
Ackermann, L ;
Kaspar, LT ;
Gschrei, CJ .
ORGANIC LETTERS, 2004, 6 (15) :2515-2518
[2]   Catalytic hydroamination of alkynes and norbornene with neutral and cationic tantalum imido complexes [J].
Anderson, LL ;
Arnold, J ;
Bergman, RG .
ORGANIC LETTERS, 2004, 6 (15) :2519-2522
[3]  
BELLER M, 1999, SYNLETT, V243
[4]   RHODIUM-CATALYZED HYDROAMINATION-HYDROARYLATION OF NORBORNENE WITH ANILINE, TOLUIDINES OR DIPHENYLAMINE [J].
BRUNET, JJ ;
COMMENGES, G ;
NEIBECKER, D ;
PHILIPPOT, K .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 469 (02) :221-228
[5]   Intramolecular hydroamination catalyzed by cationic rhodium and iridium complexes with bidentate nitrogen-donor ligands [J].
Burling, S ;
Field, LD ;
Messerle, BA ;
Turner, P .
ORGANOMETALLICS, 2004, 23 (08) :1714-1721
[6]  
CHERIAN AE, UNPUB ORG LETT
[7]   MECHANISM OF REARRANGEMENT OF N-ALKYLANILINES [J].
HART, H ;
KOSAK, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (01) :116-&
[8]  
Janssens B, 1997, STUD SURF SCI CATAL, V105, P1211
[9]  
Katwatsura M., 2000, J AM CHEM SOC, V122, P9546
[10]  
Kobayashi S, 2001, ADV SYNTH CATAL, V343, P71, DOI 10.1002/1615-4169(20010129)343:1<71::AID-ADSC71>3.3.CO