Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds

被引:157
作者
Jakhar, Vineet Kumar [1 ]
Barman, Milan Kr [1 ]
Nembenna, Sharanappa [1 ]
机构
[1] Natl Inst Sci Educ & Res, Sch Chem Sci, Bhubaneswar 752050, Orissa, India
关键词
ENANTIOSELECTIVE REDUCTION; HYDRIDE COMPLEXES; TRANSFER HYDROGENATION; ASYMMETRIC REDUCTION; KETONES; CATECHOLBORANE; ACTIVATION; ALDEHYDES; LIGANDS; METALS;
D O I
10.1021/acs.orglett.6b02310
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The well-defined aluminum monohydride compound [{(2,4,6-Me-3-C6H2)NC(Me)}(2)(Me)(H)]A1H center dot(NMe2Et) (1) catalyzes hydroboration of a wide range of aldehydes and ketones under mild reaction conditions. Moreover, compound 1 displayed chemoselective hydroboration of aldehydes over ketones at rt.
引用
收藏
页码:4710 / 4713
页数:4
相关论文
共 48 条
[1]   Coordination and Activation of Al-H and Ga-H Bonds [J].
Abdalla, Joseph A. B. ;
Riddlestone, Ian M. ;
Turner, Joshua ;
Kaufman, Paul A. ;
Tirfoin, Remi ;
Phillips, Nicholas ;
Aldridge, Simon .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17624-17634
[2]   Hydrides of the main-group metals: New variations on an old theme [J].
Aldridge, S ;
Downs, AJ .
CHEMICAL REVIEWS, 2001, 101 (11) :3305-3365
[3]   New ligands for the titanium(IV)-induced asymmetric reduction of ketones with catecholborane [J].
Almqvist, F ;
Torstensson, L ;
Gudmundsson, A ;
Frejd, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (04) :376-377
[4]   Magnesium-catalysed hydroboration of aldehydes and ketones [J].
Arrowsmith, Merle ;
Hadlington, Terrance J. ;
Hill, Michael S. ;
Kociok-Koehn, Gabriele .
CHEMICAL COMMUNICATIONS, 2012, 48 (38) :4567-4569
[5]   N-Heterocyclic Carbene Analogues with Low-Valent Group 13 and Group 14 Elements: Syntheses, Structures, and Reactivities of a New Generation of Multitalented Ligands [J].
Asay, Matthew ;
Jones, Cameron ;
Driess, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :354-396
[6]   Extremely efficient hydroboration of ketones and aldehydes by copper carbene catalysis [J].
Bagherzadeh, Sharareh ;
Mankad, Neal P. .
CHEMICAL COMMUNICATIONS, 2016, 52 (19) :3844-3846
[7]   Zinc triflate-bis-oxazoline complexes as chiral catalysts:: enantioselective reduction of α-alkoxy-ketones with catecholborane [J].
Bandini, M ;
Cozzi, PG ;
de Angelis, M ;
Umani-Ronchi, A .
TETRAHEDRON LETTERS, 2000, 41 (10) :1601-1605
[8]   Sterically Hindered Diazabutadienes (DABs): Competing Reaction Pathways with MeLi [J].
Bhadbhade, Mohan ;
Clentsmith, Guy K. B. ;
Fields, Leslie D. .
ORGANOMETALLICS, 2010, 29 (23) :6509-6517
[9]  
Blake AJ, 2000, CHEM-EUR J, V6, P3586, DOI 10.1002/1521-3765(20001002)6:19<3586::AID-CHEM3586>3.0.CO
[10]  
2-S