Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds

被引：5
|
作者：
Miyagi, Toshinori [1 ]
Okada, Sho [1 ]
Tada, Naoya [1 ]
Sugihara, Masahiro [1 ]
Kagawa, Natsuko [2 ]
Takabatake, Tetsuhiko [3 ]
Toyota, Masahiro [1 ]
机构：
[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Sakai, Osaka 5998531, Japan
[2] Chiba Univ, Ctr Environm Hlth & Field Sci, 6-2-1 Kashiwa No Ha, Kashiwa, Chiba 2770882, Japan
[3] Sumitomo Chem Co Ltd, Adv Mat Dev Lab, Konohana Ku, 1-98 Kasugadenaka,3 Chome, Osaka 5548558, Japan
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 25期
关键词：
Palladium acetate; Orthogonal synthesis; 2-Hydroxybenzoate; Substituted cyclohexanone; CATALYZED INTRAMOLECULAR HYDROALKYLATION; FREE-RADICAL CYCLIZATIONS; BETA-KETO-ESTERS; C-H BONDS; OXIDATIVE CYCLIZATION; PALLADIUM; CYCLOALKENYLATION; CONSTRUCTION; DERIVATIVES; MECHANISM;
D O I：
10.1016/j.tetlet.2019.05.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)(2) and Cu(OAc)(2). On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)(2) and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1653 / 1657
页数：5
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