Synthesis of Carbamates by Direct C-H Bond Activation of Formamides

被引：41

作者：

Barve, Balaji D. ^{[1
,2
]}

Wu, Yang-Chang ^{[2
,3
,4
,5
]}

El-Shazly, Mohamed ^{[2
,6
]}

Chuang, Da-Wei ^{[2
]}

Chung, Yu-Ming ^{[2
]}

Tsai, Yi-Hong ^{[2
]}

Wu, Shou-Fang ^{[2
]}

Korinek, Michal ^{[2
]}

Du, Ying-Chi ^{[2
]}

Hsieh, Chi-Ting ^{[2
]}

Wang, Jeh-Jeng ^{[1
]}

Chang, Fang-Rong ^{[2
,7
,8
,9
]}

机构：

[1] Kaohsiung Med Univ, Coll Life Sci, Dept Med & Appl Chem, Kaohsiung 807, Taiwan

[2] Kaohsiung Med Univ, Coll Pharm, Grad Inst Nat Prod, Kaohsiung 807, Taiwan

[3] China Med Univ Hosp, Ctr Mol Med, Taichung 404, Taiwan

[4] China Med Univ, Coll Chinese Med, Sch Chinese Med, Taichung 404, Taiwan

[5] China Med Univ Hosp, Nat Med Prod Res Ctr, Taichung 404, Taiwan

[6] Ain Shams Univ, Org African Unity, Fac Pharm, Dept Pharmacognosy & Nat Prod Chem, Cairo, Egypt

[7] Kaohsiung Med Univ Hosp, Ctr Canc, Kaohsiung 807, Taiwan

[8] Kaohsiung Med Univ, Coll Pharm, R&D Ctr Chinese Herbal Med & New Drugs, Kaohsiung 807, Taiwan

[9] Natl Sun Yat Sen Univ, Dept Marine Biotechnol & Resources, Kaohsiung 804, Taiwan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 34期

关键词：

Synthetic methods; Oxidation; C-H activation; Regioselectivity; Carb-amates; Copper; MONOXIDE-FREE AMINOCARBONYLATION; NATURAL-PRODUCTS; ARYL; CYANATION; AMINES; ALKYL; N; N-DIMETHYLFORMAMIDE; REARRANGEMENT; EFFICIENT; FORMYLOXY;

D O I：

10.1002/ejoc.201201160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper catalysed oxidative coupling reaction of formamides with beta-keto esters and 2-carbonyl-substituted phenols successfully proceeded through direct CH bond activation of formamides. The corresponding carbamates were formed with high stereoselectivity under mild reaction conditions. This protocol was successfully applied to the synthesis of three novel halogenated carbamates and a carbaryl insecticide derivative. Our results suggest the use of 6.0 equiv. TBHP is crucial for this type of reaction.

引用

页码：6760 / 6766

页数：7

共 62 条

[1]

[Anonymous], ULLMANNS ENCY IND CH

[2] One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates [J].