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Cover Picture: Biomimetic Aerobic CH Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5‐Trisubstituted Benzenes (Adv. Synth. Catal. 6/2014)
Author(s) -
Yu YiYun,
Georg Gunda I.
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400050
Subject(s) - chemistry , tandem , surface modification , oxygen atom , combinatorial chemistry , annulation , palladium , stereochemistry , organic synthesis , catalysis , organic chemistry , molecule , materials science , composite material
The front cover picture , provided by Yi‐Yun Yu and Gunda I. Georg, illustrates a novel synthesis of 1,3,5‐trisubstituted benzenes from cyclic enaminones featuring a CH functionalization and Diels‐Alder tandem sequence. First, the enaminone dienes were constructed atom‐economically by a dehydrogenative cross‐olefination. This palladium‐catalyzed biomimetic CH coupling uses oxygen as the terminal oxidant and proceeds smoothly at room temperature. Then, the enaminone dienes underwent a Diels‐Alder tandem reaction to furnish distinct 1,3,5‐trisubstituted benzenes, including chalcones, with easily controllable symmetry. This new protocol provides an alternative pathway for arene functionalization. The details are disclosed in the Update by Yu and Georg on pages 1359–1369 (Y.‐Y. Yu, G. I. Georg, Adv. Synth. Catal. 2014, 356, 1359–1369; DOI: 10.1002/adsc.201300904) .