Rhodium-Catalyzed Anti-Markovnikov Hydroamination of Aliphatic and Aromatic Terminal Alkynes with Aliphatic Primary Amines

被引:8
作者
Morimoto, Yoshihiko [1 ]
Kochi, Takuya [1 ]
Kakiuchi, Fumitoshi [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Yokohama, Kanagawa 2238522, Japan
关键词
INTERMOLECULAR HYDROAMINATION; SECONDARY-AMINES; CYCLOPENTADIENYL LIGAND; GENERAL CATALYST; PENDANT ETHER; COMPLEXES; SUBSTITUENT; ARYLACETYLENES; ALCOHOLS; BEHAVIOR;
D O I
10.1021/acs.joc.1c01636
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anti-Markovnikov hydroamination of both aliphatic and aromatic terminal alkynes with primary amines was achieved using an 8-quinolinolato rhodium catalyst to form aldimines and enamines in high yields. This catalytic system realized high functional group tolerance including hydroxy, bromo, cyano, and thioester groups.
引用
收藏
页码:13143 / 13152
页数:10
相关论文
共 54 条
[1]   Well-Defined Regioselective Iminopyridine Rhodium Catalysts for Anti-Markovnikov Addition of Aromatic Primary Amines to 1-Octyne [J].
Alonso-Moreno, Carlos ;
Carrillo-Hermosilla, Fernando ;
Romero-Fernandez, Javier ;
Rodriguez, Ana M. ;
Otero, Antonio ;
Antinolo, Antonio .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) :881-890
[2]   CATALYTIC AND NON-CATALYTIC ADDITION OF AROMATIC-AMINES TO TERMINAL ACETYLENES IN THE PRESENCE OF MERCURY(II) CHLORIDE AND ACETATE [J].
BARLUENGA, J ;
AZNAR, F ;
LIZ, R ;
RODES, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (12) :2732-2737
[3]   An (Aminopyrimidinato)titanium Catalyst for the Hydroamination of Alkynes and Alkenes [J].
Brahms, Christian ;
Tholen, Patrik ;
Saak, Wolfgang ;
Doye, Sven .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (33) :7583-7592
[4]   Preparation and X-ray structures of alkyl-titanium(IV) complexes stabilized by indenyl ligands with a pendant ether or amine substituent and their use in the catalytic hydroamination of alkynes [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Lopez, Ana M. ;
Mateo, A. Concepcion ;
Onate, Enrique .
ORGANOMETALLICS, 2007, 26 (03) :554-565
[5]   Preparation of half-sandwich alkyl-titanium(IV) complexes stabilized by a cyclopentadienyl ligand with a pendant phosphine tether and their use in the catalytic hydroamination of aliphatic and aromatic alkynes [J].
Buil, Maria L. ;
Esteruelas, Miguel A. ;
Lopez, Ana M. ;
Mateo, A. Concepcion .
ORGANOMETALLICS, 2006, 25 (17) :4079-4089
[6]   Catalyst Evolution in Ruthenium-Catalyzed Coupling of Amines and Alcohols [J].
Cherepakhin, Valeriy ;
Williams, Travis J. .
ACS CATALYSIS, 2020, 10 (01) :56-65
[7]   New half-sandwich alkyl, aryl, aryloxide, and propargyloxide titanium(IV) complexes containing a cyclopentadienyl ligand with a pendant ether substituent:: Behavior and influence in the hydroamination of alkynes of the ether group [J].
Esteruelas, MA ;
López, AM ;
Mateo, AC ;
Oñate, E .
ORGANOMETALLICS, 2006, 25 (06) :1448-1460
[8]   New titanium complexes containing a cyclopentadienyl ligand with a pendant aminoalkyl substituent:: Preparation, behavior of the amino group, and catalytic hydroamination of alkynes [J].
Esteruelas, MA ;
López, AM ;
Mateo, AC ;
Oñate, E .
ORGANOMETALLICS, 2005, 24 (21) :5084-5094
[9]   Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes [J].
Evano, Gwilherm ;
Gaumont, Annie-Claude ;
Alayrac, Carole ;
Wrona, Iwona E. ;
Giguere, Joshua R. ;
Delacroix, Olivier ;
Bayle, Alexandre ;
Jouvin, Kevin ;
Theunissen, Cedric ;
Gatignol, Jeremie ;
Silvanus, Andrew C. .
TETRAHEDRON, 2014, 70 (08) :1529-1616
[10]   Anti-markovnikov addition of both primary and secondary Amines to terminal Alkynes catalyzed by the TpRh(C2H4)2/PPh3 system [J].
Fukumoto, Yoshiya ;
Asai, Harumi ;
Shimizu, Masaki ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13792-+