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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.
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页码:8756 / 8867
页数:112
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