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Frontispiece: The Mechanism of Copper‐Catalyzed Trifunctionalization of Terminal Allenes
Author(s) -
Kim Hong Ki,
Mane Manoj V.,
Montgomery John,
Baik MuHyun
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201984065
Subject(s) - cyanation , electrophile , catalysis , chemistry , copper , medicinal chemistry , regioselectivity , terminal (telecommunication) , reaction mechanism , combinatorial chemistry , stereochemistry , organic chemistry , computer science , telecommunications
A new method for tri‐functionalizing allenes was successfully developed based on diborylation/cyanation with bis(pinacolato)diboron (B 2 pin 2 ) and N ‐cyano‐ N ‐phenyl‐ p ‐toluenesulfonamide (NCTS). This Cu‐catalyzed reaction comprises of three catalytic reactions (1st borocupration, electrophilic cyanation, and 2nd borocupration) that provide a densely functionalized product with regio‐, chemo‐ and diastereoselectivity. DFT calculations explain how the outstanding regio‐, chemo‐ and diastereoselectivity is achieved. For more information, see the Full Paper by M.‐H. Baik et al. on page 9456 ff.