Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

被引:276
作者
Campeau, Dominic [1 ]
Rayo, David F. Leon [1 ]
Mansour, Ali [1 ]
Muratov, Karim [1 ]
Gagosz, Fabien [1 ]
机构
[1] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
INTERMOLECULAR NITRENE TRANSFER; FORMAL 3+2 CYCLOADDITION; N-HETEROCYCLIC CARBENE; CYCLIZATION-OXIDATIVE ALKYNYLATION; UGI INTRAMOLECULAR HYDROARYLATION; ELECTRON-DEFICIENT ALKYNES; HIGHLY EFFICIENT SYNTHESIS; ATOM-ECONOMICAL SYNTHESIS; C-H ALKYNYLATION; REGIOSELECTIVE SYNTHESIS;
D O I
10.1021/acs.chemrev.0c00788
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon p-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon p-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon p-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon p-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon p-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.
引用
收藏
页码:8756 / 8867
页数:112
相关论文
共 475 条
[1]   Gold-Catalyzed Highly Chemo- and Regioselective C-H Bond Functionalization of Phenols with Haloalkynes [J].
Adak, Tapas ;
Schulmeister, Juergen ;
Dietl, Martin C. ;
Rudolph, Matthias ;
Rominger, Frank ;
Hashmi, A. Stephen K. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (24) :3867-3876
[2]   Two tandem sequential reactions catalyzed by [Au], N-heterocyclic carbenes (NHC) and organic bases [J].
Adamo, Mauro F. A. ;
Bellini, Gea ;
Suresh, Surisetti .
TETRAHEDRON, 2011, 67 (32) :5784-5788
[3]   Divergent C-H Insertion-Cyclization Cascades of N-Allyl Ynamides [J].
Adcock, Holly V. ;
Chatzopoulou, Elli ;
Davies, Paul W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) :15525-15529
[4]   1,2-N-Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides [J].
Adcock, Holly V. ;
Langer, Thomas ;
Davies, Paul W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) :7262-7266
[5]   A Formal Enantioselective Synthesis of (-)-Epiquinamide by Proline-Catalyzed One-Pot Sequential -Amination/Propargylation of Aldehyde and Asymmetric Dihydroxylation of Olefin [J].
Ahuja, Brij Bhushan ;
Emmanuvel, Lourdusamy ;
Sudalai, Arumugam .
SYNLETT, 2016, 27 (11) :1699-1702
[6]   A facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones [J].
Akram, Manjur O. ;
Bera, Saibal ;
Patil, Nitin T. .
CHEMICAL COMMUNICATIONS, 2016, 52 (83) :12306-12309
[7]   Mechanistic Studies of Gold and Palladium Cooperative Dual-Catalytic Cross-Coupling Systems [J].
Al-Amin, Mohammad ;
Roth, Katrina E. ;
Blum, Suzanne A. .
ACS CATALYSIS, 2014, 4 (02) :622-629
[8]   Regiodivergent Control in the Gold(I) Catalyzed Synthesis of 7-Pyrazolylindoles from 1-Propargyl-1H-benzotriazoles and Ynamides through α-Imino Gold(I) Carbene Complexes [J].
Allegue, Dario ;
Gonzalez, Jairo ;
Fernandez, Sergio ;
Santamaria, Javier ;
Ballesteros, Alfredo .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (04) :758-768
[9]   Platinum and Gold Catalysis: a la Carte Hydroamination of Terminal Activated Allenes with Azoles [J].
Alonso, Jose Miguel ;
Munoz, Maria Paz .
ORGANIC LETTERS, 2019, 21 (18) :7639-7644
[10]   Gold as a catalyst. Part III. Addition to double bonds [J].
Alyabyev, Sergey B. ;
Beletskaya, Irina P. .
RUSSIAN CHEMICAL REVIEWS, 2020, 89 (05) :491-536