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Transition‐Metal‐Catalyzed Direct Addition of Aryl C–H Bonds to Unsaturated Electrophiles
Author(s) -
Shi XianYing,
Han WenJing,
Li ChaoJun
Publication year - 2016
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201500250
Subject(s) - electrophile , aryl , catalysis , transition metal , chemistry , electrophilic addition , metal , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
The direct addition of Csp 2 –H bonds onto polar C=C, C=O, and C=N bonds is both synthetically and mechanistically important, because using aromatic C–H substrates in place of organometallic reagents provides a more direct and atom‐economical alternative to many important compounds without the pre‐generation of organometallic compounds from stoichiometric halides and the unavoidable generation of stoichiometric metal halide waste. In this account, we summarize our contributions to the transition‐metal‐catalyzed addition of aromatic C–H bonds to polar C=C, C=O, and C=N bonds via directing‐group‐assisted regiospecific reactions. These synthetic methods provide efficient access to benzylic alcohols, alkylbenzenes, 3‐substituted phthalides, N ‐substituted phthalimides, N ‐aryl benzamides, and indene derivatives from commercially available reagents. It is worth noting that valuable heterocycles such as 3‐substituted phthalides and N ‐substituted phthalimides can be obtained in one step by this approach.