Reactivity of Morita-Baylis-Hillman Adducts in C-H Functionalization of (Hetero)aryl Nitrones: Access to Bridged Cycles and Carbazoles

被引：29

作者：

Pandey, Ashok Kumar ^{[1
]}

Kang, Dahye ^{[2
,3
]}

Han, Sang Hoon ^{[1
]}

Lee, Heeyoung ^{[1
]}

Mishra, Neeraj Kumar ^{[1
]}

Kim, Hyung Sik ^{[1
]}

Jung, Young Hoon ^{[1
]}

Hong, Sungwoo ^{[2
,3
]}

Kim, In Su ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Suwon 16419, South Korea

[2] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea

[3] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 34141, South Korea

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

N-HETEROCYCLES; ACTIVATION; ALLYLATION; ALKYNES; ARYLNITRONES; CYCLIZATION; ANNULATION; CATALYSIS; INDOLES; ARENES;

D O I：

10.1021/acs.orglett.8b01910

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rhodium(III)-catalyzed cross-coupling of (hetero)aryl nitrones with Morita-Baylis-Hillman (MBH) adducts is described. An allylated intermediate derived from aryl nitrones and MBH adducts allows the formation of bridged cyclic compounds via an exotype [3 + 2] cycloaddition. In sharp contrast, electron-rich indolinyl or aniline substrates were found to couple with MBH adducts to generate naphthalene or carbazole derivatives, respectively.

引用

页码：4632 / 4636

页数：5

共 26 条

[21] Facile Regio- and Stereoselective Metal-Free Synthesis of All-Carbon Tetrasubstituted Alkenes Bearing a C(sp3)-F Unit via Dehydroxyfluorination of Morita-Baylis-Hillman (MBH) Adducts
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[25] First construction of 12H-thiochromeno[2,3-b]quinolines and 5H-benzo[7,8] thiocino-[2,3-b]quinolines via intramolecular Friedel-Crafts reaction of Morita-Baylis-Hillman adducts
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[26] Enantioselective catalysis of intramolecular Morita-Baylis-Hillman and related reactions by chiral rhenium-containing phosphines of the formula (η5-C5H5)Re(NO)(PPh3)(CH2PAr2)
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