Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers
作者:Thomas Kunz、Paul Knochel
DOI:10.1002/anie.201106734
日期:2012.2.20
Highly functional: A copper(I)‐catalyzed intramolecularcarbomagnesiation under mild conditions transforms readily available alkynyl(aryl)thioethers into magnesiated benzothiophenes. Subsequent reaction with various electrophiles (acid chlorides, allyl bromides, aryl halides) provides polyfunctional benzo[b]thiophenes (see scheme). Further modification of the cyclization products affords highly diversified
高度功能化:在温和条件下,铜(I)催化的分子内碳镁化作用可将易得的炔基(芳基)硫醚转变成镁化的苯并噻吩。随后与各种亲电试剂(酰氯,烯丙基溴,芳基卤化物)反应,可得到多官能的苯并[ b ]噻吩(请参见方案)。环化产物的进一步修饰提供了高度多样化的苯并噻吩衍生物和新的杂环支架。
Palladium-Catalyzed [4 + 3] or [2 + 2 + 3] Annulation via C–H Activation and Subsequent Decarboxylation: Access to Heptagon-Embedded Polycyclic Aromatic Hydrocarbons
attractive challenge. Herein a novel palladium-catalyzed [4 + 3] decarboxylative annulation of 2-iodobiphenyls with 2-(2-halophenyl)acrylic acids is reported, which provides an efficient approach for assembling various tribenzo[7]annulenes via a C–H activation and decarboxylation process. Moreover, tribenzo[7]annulenes can be also synthesized via a [2 + 2 + 3] decarboxylative annulation strategy by employing
Pd/Cu-Catalyzed Cascade C(sp<sup>3</sup>)–H Arylation and Intramolecular C–N Coupling: A One-Pot Synthesis of 3,4-2<i>H</i>-Quinolinone Skeletons
作者:Han-Zhi Xiao、Wen-Shu Wang、Yu-Song Sun、Hao Luo、Bo-Wen Li、Xiao-Dong Wang、Wei-Li Lin、Fei-Xian Luo
DOI:10.1021/acs.orglett.9b00214
日期:2019.3.15
In this letter, we successfully explored a cascade Pd/Cu-catalyzed intermolecular C(sp3)–H arylation of amides and intramolecular C–N coupling reaction. This method provides a one-pot strategy to synthesize 3,4-2H-quinolinone with good regioselectivity of C–H arylation and C–N coupling from C–I and C–X bonds from readily available starting materials.
The first example of catalytic enantioselective tautomerization of structurally labile but isolable enamines for accessing their chiral imine-tautomers is described. Kinetically stable enamine-based dibenzo[b,d]azepines were tautomerized by a simple chiral BINOL–phosphoric acid, providing a variety of seven-membered imine products bearing both central and axial stereogenic elements in good yields (up
A chemo- and regioselective Pd(0)-catalyzed spiroannulation has been successfully developed. The key feature of this method is the use of readily available 1,2-dihaloarenes, alkynes and 2-naphthols for the rapid assembly of spirocarbocyclic molecules. Mechanistic studies revealed that this domino reaction proceeded through a cascade of oxidative addition to Pd(0), alkyne migratory insertion, and 2