银 triflate 催化 2-炔基苯甲醛肟与芳炔的反应。
Silver triflate catalyzed reaction of 2-alkynylbenzaldoxime with aryne.
机构信息
Department of Chemistry, Fudan University, Shanghai, China.
出版信息
Org Lett. 2011 May 20;13(10):2552-5. doi: 10.1021/ol200629y. Epub 2011 Apr 1.
PMID:21456516
Abstract
A novel and unexpected reaction of 2-alkynylbenzaldoxime with aryne in the presence of silver triflate (10 mol %) under mild conditions is discovered. This reaction proceeds through 6-endo-cyclization, [3 + 2] cycloaddition, and rearrangement, leading to 2-oxa-6-aza-bicyclo[3.2.2]nona-6,8-diene derivatives in moderate to good yields.
摘要
在温和条件下，研究人员发现了 2-炔基苯甲肟与芳基在三氟甲磺酸银（10mol%）存在下的一种新颖且出人意料的反应。该反应通过 6-endo-环化、[3+2]环加成和重排进行，从而以中等至良好的收率得到 2-氧杂-6-氮杂双环[3.2.2]壬-6,8-二烯衍生物。
相似文献
1
Silver triflate catalyzed reaction of 2-alkynylbenzaldoxime with aryne.银 triflate 催化 2-炔基苯甲醛肟与芳炔的反应。
Org Lett. 2011 May 20;13(10):2552-5. doi: 10.1021/ol200629y. Epub 2011 Apr 1.
2
An unexpected silver triflate-catalyzed tandem reaction of N'-(2-alkynylbenzylidene)hydrazide with ketene.银 triflate 催化的 N'-(2-炔基苯亚甲基)腙与烯酮的串联反应
Chem Commun (Camb). 2012 Jul 18;48(56):7049-51. doi: 10.1039/c2cc33375a. Epub 2012 Jun 8.
3
An efficient route to 1-aminoisoquinolines via AgOTf-catalyzed reaction of 2-alkynylbenzaldoxime with amine.AgOTf 催化 2-炔基苯甲醛肟与胺反应高效构建 1-氨基异喹啉类化合物的新途径。
Org Biomol Chem. 2011 Jul 7;9(13):4763-5. doi: 10.1039/c1ob05582h. Epub 2011 May 26.
4
An unexpected silver triflate catalyzed reaction of 2-alkynylbenzaldehyde with 2-isocyanoacetate.银 triflate 催化 2-炔基苯甲醛与 2-异氰基乙酸酯的意外反应。
Org Lett. 2012 Jun 1;14(11):2655-7. doi: 10.1021/ol300901x. Epub 2012 May 22.
5
A silver(I) triflate-catalyzed reaction of 1-((cyclopropylidenemethyl)-2-alkynyl)arene with 2-alkynylbenzaldoxime.三氟甲磺酸银（I）催化的1-（（环丙基亚甲基）-2-炔基）芳烃与2-炔基苯甲醛肟的反应。
Chem Commun (Camb). 2014 Apr 25;50(32):4188-91. doi: 10.1039/c4cc00691g.
6
Silver triflate and palladium acetate co-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with N-allyl ynamide.银 triflate 和醋酸钯共催化 N'-(2-炔基苯亚甲基)腙与 N-烯丙基炔酰胺的反应。
Org Lett. 2012 Jun 1;14(11):2790-3. doi: 10.1021/ol301023m. Epub 2012 May 22.
7
A silver(I)-catalyzed tandem reaction of 2-alkynylbenzaldoximes with ketenes.银（I）催化的 2-炔基苯甲醛肟与烯酮的串联反应。
Org Biomol Chem. 2013 May 7;11(17):2898-902. doi: 10.1039/c3ob27427f. Epub 2013 Mar 21.
8
Construction of Azabicyclo[6.4.0]dodecatrienes Based on Rhodium(I)-Catalyzed Intramolecular [6+2] Cycloaddition between Azetidine, Allene, and Alkynes.基于铑（I）催化的氮杂环丁烷、丙二烯和炔烃之间的分子内[6+2]环加成反应构建氮杂双环[6.4.0]十二碳三烯
Chem Pharm Bull (Tokyo). 2016;64(7):805-10. doi: 10.1248/cpb.c16-00178.
9
Ytterbium(III) triflate catalyzed tandem Friedel-Crafts alkylation/hydroarylation of propargylic alcohols with phenols as an expedient route to indenols.三氟甲磺酸镱（III）催化炔丙醇与酚的串联傅克烷基化/氢芳基化反应，是合成茚醇的便捷途径。
Org Lett. 2009 Nov 5;11(21):4990-3. doi: 10.1021/ol901981s.
10
Silver triflate catalyzed tandem heterocyclization/alkynylation of 1-((2-tosylamino)aryl)but-2-yne-1,4-diols to 2-alkynyl indoles.三氟甲磺酸银催化的 1-((2-对甲苯磺酰氨基)芳基)丁-2-炔-1,4-二醇的串联杂环化/炔基化反应生成 2-炔基吲哚。
Chemistry. 2012 May 14;18(20):6133-7. doi: 10.1002/chem.201200578. Epub 2012 Apr 18.
引用本文的文献
1
Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones.利用钯催化的酮的α-芳基化反应合成取代的异喹啉。
Proc Natl Acad Sci U S A. 2012 Jul 17;109(29):11605-8. doi: 10.1073/pnas.1206532109. Epub 2012 Jul 2.
2
Generation of diverse 1-imidazolylisoquinolines via silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime with imidazole.通过银三氟甲磺酸酯催化 2-炔基苯甲醛肟与咪唑的反应生成多样的 1-咪唑基异喹啉。
Mol Divers. 2012 May;16(2):261-8. doi: 10.1007/s11030-012-9355-4. Epub 2012 Jan 25.
Zotero 插件