Neutral Ti catalysts for the intramolecular hydroamination of alkenes

被引：73

作者：

Mueller, Carsten ^{[1
]}

Loos, Christian ^{[1
]}

Schulenberg, Nikola ^{[1
]}

Doye, Sven ^{[1
]}

机构：

[1] Univ Heidelberg, Organ Chem Inst, D-69120 Heidelberg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 11期

关键词：

alkenes; amines; homogeneous catalysis; hydroamination; titanium;

D O I：

10.1002/ejoc.200600115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Neutral titanium complexes are well known precatalysts for the inter- and intramolecular hydroamination of alkynes. In this publication, we show the capability of several neutral titanium complexes to catalyze intramolecular hydroamination reactions of alkenes. The corresponding pyrrolidine and piperidine products are formed in yields up to 97%. Among the substrates used, only geminally disubstituted amino alkenes are successfully cyclized.

引用

页码：2499 / 2503

页数：5

共 54 条

[1] TiCl4-catalyzed intermolecular hydroamination reactions of norbornene
Ackermann, L
Kaspar, LT
Gschrei, CJ
[J]. ORGANIC LETTERS, 2004, 6 (15) : 2515 - 2518
[2] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes
Ackermann, L
Bergman, RG
Loy, RN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) : 11956 - 11963
[3] Proton-catalyzed hydroamination and hydroarylation reactions of anilines and alkenes: A dramatic effect of counteranions on reaction efficiency
Anderson, LL
Arnold, J
Bergman, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) : 14542 - 14543
[4] Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines
Bender, CF
Widenhoefer, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) : 1070 - 1071
[5] TITANOCENE AS AN INTERMEDIATE IN REACTIONS INVOLVING MOLECULAR-HYDROGEN AND NITROGEN
BERCAW, JE
BELL, LG
BRINTZIN.HH
MARVICH, RH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (04) : 1219 - &
[6] Intramolecular hydroamination of unactived olefins with Ti(NMe2)4 as a precatalyst
Bexrud, JA
Beard, JD
Leitch, DC
Schafer, LL
[J]. ORGANIC LETTERS, 2005, 7 (10) : 1959 - 1962
[7] Brunet J.J., 2001, CATALYTIC HETEROFUNC, P91
[8] Intermolecular highly regioselective hydroamination of alkenes with ligandless Platinum(II) catalysts in ionic solvents:: Activation role of n-Bu4PBr
Brunet, JJ
Chu, NC
Diallo, O
[J]. ORGANOMETALLICS, 2005, 24 (13) : 3104 - 3110
[9] Bytschkov I, 2003, EUR J ORG CHEM, V2003, P935
[10] Application of amine elimination for the efficient preparation of electrophilic ansa-monocyclopentadienyl group 4 complexes containing an appended amido functionality. Structural characterization of [(C5H4) SiMe(2)(N-t-Bu)] ZrCl2 (NMe(2)H)
Carpenetti, DW
Kloppenburg, L
Kupec, JT
Petersen, JL
[J]. ORGANOMETALLICS, 1996, 15 (06) : 1572 - 1581

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