3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light

被引:116
作者
Bosque, Irene [1 ,2 ,3 ]
Bach, Thorsten
机构
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
[2] Univ Alicante, Organ Chem Dept, Inst Electrochem, Carretera San Vicente Raspeig S-N, Alicante 03690, Spain
[3] Univ Alicante, Inst Organ Synth, Carretera San Vicente Raspeig S-N, Alicante 03690, Spain
关键词
electron donor acceptor complex; photochemistry; 3-acetoxyquinuclidine; homogeneous catalysis; tetrachlorophthalimide; BOND-DISSOCIATION ENERGIES; REDOX-ACTIVE ESTERS; PHOTOCHEMICAL ACTIVITY; ALPHA-ALKYLATION; MECHANISM;
D O I
10.1021/acscatal.9b01039
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
3-Acetoxyquinuclidine was found to act as a catalytic electron donor species in a variety of electron donor-acceptor complex-mediated reactions. Only substoichiometric amounts (10-25 mol %) were needed to trigger the desired reaction. The outcome could be tuned by selecting the nature of the formed radical to perform amino and hydro-decarboxylation, dimerization, and cyclization reactions. Importantly, no external additives were needed in this reaction.
引用
收藏
页码:9103 / 9109
页数:13
相关论文
共 35 条
[1]  
Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]
[2]   Mechanism of the Stereoselective α-Alkylation of Aldehydes Driven by the Photochemical Activity of Enamines [J].
Bahamonde, Ana ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (25) :8019-8030
[3]   Chromophore Activation of α,β-Unsaturated Carbonyl Compounds and Its Application to Enantioselective Photochemical Reactions [J].
Brenninger, Christoph ;
Jolliffe, John D. ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (44) :14338-14349
[4]   Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters [J].
Candish, Lisa ;
Teders, Michael ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (22) :7440-7443
[5]   Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex [J].
Cao, Zhong-Yan ;
Ghosh, Tamal ;
Melchiorre, Paolo .
NATURE COMMUNICATIONS, 2018, 9
[6]   Photoinduced decarboxylative borylation of carboxylic acids [J].
Fawcett, Alexander ;
Pradeilles, Johan ;
Wang, Yahui ;
Mutsuga, Tatsuya ;
Myers, Eddie L. ;
Aggarwal, Varinder K. .
SCIENCE, 2017, 357 (6348) :283-286
[7]   ELECTRON DONOR-ACCEPTOR COMPLEXES [J].
FOSTER, R .
JOURNAL OF PHYSICAL CHEMISTRY, 1980, 84 (17) :2135-2141
[8]   UNIFIED MECHANISM FOR THERMAL AND PHOTO-CHEMICAL ACTIVATION OF CHARGE-TRANSFER PROCESSES WITH ORGANOMETALS - STERIC EFFECTS IN THE INSERTION OF TETRACYANOETHYLENE [J].
FUKUZUMI, S ;
MOCHIDA, K ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) :5961-5972
[9]   BOND DISSOCIATION ENERGIES IN SOME MOLECULES CONTAINING ALKYL SUBSTITUTED CH3, NH2 AND OH [J].
GOWENLOCK, B ;
JONES, PP ;
MAJER, JR .
TRANSACTIONS OF THE FARADAY SOCIETY, 1961, 57 (01) :23-&
[10]  
Hodge Markgraf J., 1997, TETRAHEDRON, V53, P10009