Palladium‐Catalyzed Allylic Arylation of Allylic Ethers with Arylboronic Acids Using Hydrazone Ligands. Issue 8 (29th January 2013)

• Record Type: Journal Article
• Authors: Mino, Takashi; Kogure, Taketo; Abe, Taichi; Koizumi, Tomoko; Fujita, Tsutomu; Sakamoto, Masami
• Is Part Of: European journal of organic chemistry. Issue 8(2013)
• Page Start: 1501
• Page End: 1505
• Publication Date: 2013-01-29
• Subjects: Palladium -- Hydrazones -- Cross‐coupling -- N ligands -- Homogeneous catalysis­ -- Arylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201276
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Unsymmetrical 1, 3‐diarylpropenes were synthesized in good to high yields by the palladium‐catalyzed allylic arylation of allylic ethers, such as a cinnamyl phenyl ether, with a variety of arylboronic acids using a hydrazone1a –Pd(OAc)2 system in DMAc/H2 O. Using this catalyst, eugenol was also synthesized from allyl phenyl ether with (4‐hydroxy‐3‐methoxyphenyl)boronic acid pinacol ester. Abstract : A palladium‐catalyzed allylic arylation of cinnamyl phenyl ether derivatives with a variety of arylboronic acids using 5 mol‐% of a hydrazone1a –Pd(OAc)2 system in DMAc/H2 O at 50 °C gave 1, 3‐diarylpropenes in good yields. We also succeeded with the synthesis of eugenol by a palladium‐catalyzed allylic arylation.