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A Convenient Preparative Method for New 1,3‐Bis(hetaryl)‐2‐chloropropen‐1‐ones Using β‐Alkoxy‐α‐chloroalkenyllithium Compounds
Author(s) -
Itoh Akinori,
Sakai Miho,
Yoshimatsu Mitsuhiro
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600957
Subject(s) - chemistry , alkoxy group , palladium , organic chemistry , medicinal chemistry , reaction conditions , catalysis , alkyl
The 1,3‐biaryl and 1,3‐bis(hetaryl)propen‐1‐ones 14a – e , 16 , 17a – c , 19 , 20a and the corresponding acetals 15a – d , 18a and 21a – d were successfully synthesized by a stepwise process: the reaction of α‐chloro‐β‐ethoxyethenyllithium compounds and aldehydes and ketones, and the successive hydration with TMSOTf. Further palladium‐catalyzed arylation of 1,3‐biaryl‐2‐chloroprop‐2‐enones proceeded with good yields.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)