Research advances in palladium-catalysed intermolecular C–H annulation of aryl halides with various aromatic ring precursors

Qiao, Shujia; Deng, Wenbo; Deng, Guobo; Liang, Yun; Yang, Yuan

doi:10.1039/d2ob01129h

Cited by 11 publications

(2 citation statements)

References 113 publications

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“…Our group has an ongoing interest in palladium-catalyzed cascade C–H cyclization by trapping five-membered C , C -palladacycles with coupling reagents, which provides an efficient platform for the synthesis of polycyclic compounds. − Since the pioneering work was reported by Lautens and co-workers, great advances have been made by employing various coupling reagents as C or N sources. , Nevertheless, the incorporation of Si- or Si,O-containing sources into substrates for assembling silacycles remains elusive. Given this challenge, our group recently developed a new disilane reagent Me 3 SiSiMe 2 (O n Bu), which enabled the synthesis of five-membered silacycles via a palladium-catalyzed C–H disilylation and the Brook rearrangement strategy.…”

Section: Introductionmentioning

confidence: 99%

Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C–H Activation

Sun

et al. 2023

J. Am. Chem. Soc.

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Transition-metal-catalyzed intermolecular annulation of silicon reagents with organic molecules is still underdeveloped due to the scarcity of silicon reagent types and their diverse reactivity. Herein, a readily accessible silicon reagent (octamethyl-1,4-dioxacyclohexasilane) has been developed for divergent synthesis of silacycles via time-controlled palladiumcatalyzed cascade C−H silacyclization. This protocol enables the rapid and selective transformation of acrylamides into spirosilacycles with different ring sizes, including benzodioxatetrasilecines, benzooxadisilepines, and benzosiloles, in moderate to good yields through a time switch. Notably, the tetrasilane reagent can also be utilized for C−H silacyclization of 2-halo-Nmethacryloylbenzamides and 2-iodobiphenyls, leading to diverse fused silacycles. Furthermore, several synthetic transformations of products are achieved. A series of mechanistic studies demonstrate the transformation relationships and possible pathways among ten-, seven-, and five-membered silacycles.

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Section: Introductionmentioning

confidence: 99%

Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C–H Activation

Sun

et al. 2023

J. Am. Chem. Soc.

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“…On one hand, cascade reactions have emerged as a powerful method for the construction of complex organic molecules due to its high efficiency and step economy . On the other hand, five-membered C , C -palladacycles as key intermediates have attracted considerable attention owing to not only the existing C–H activation but also their versatile conversions in which two C–Pd bonds could be functionalized by reacting with coupling partners. , For these reasons, palladium-catalyzed cascade reactions involving five-membered C , C -palladacycles are of extraordinary interest to synthetic chemists . A typical method is carbopalladation/C–H functionalization of alkene- or alkyne-tethered aryl halides.…”

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confidence: 99%

Pd(II)-Catalyzed Synthesis of Polycyclic Heteroarenes via an Aminopalladation/C–H Activation/Dealkylation/Decarboxylative Cyclization Cascade

Chen

et al. 2022

Org. Lett.

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Until now, cascade reactions involving five-membered C,C-palladacycles rely heavily on Pd(0)-catalyzed C–H functionalization of aryl halides initiated by carbopalladation. Herein, we report a novel Pd(II)-catalyzed cascade decarboxylative cyclization of o-alkynylanilines initiated by aminopalladation. In this protocol, o-alkynylanilines undergo sequential anti aminopalladation, C–H activation, and dealkylation to form C,C-palladacycles, which are then trapped by o-bromobenzoic acids or 8-bromo-1-naphthoic acid to produce diverse polycyclic heteroarenes, such as dibenzo[a,c]carbazoles and multiple arene-fused cyclohepta[1,2-b]indoles.

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Pd/Cu Co‐Catalyzed ortho‐Arylation of Aryl Iodides via Radical Intermediates with Aryl Diazonium Salts

Fu,

Guo,

Chen

et al. 2023

Adv Synth Catal

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A Cu/Pd co‐catalyzed Catellani‐type ortho arylation reaction of iodoarenes with aryl diazonium salts has been developed. Aryl radicals that derived from aryl diazonium salts were regioselectively installed at ortho position of iodoarenes via palladium catalyzed C−H activation. Mechanistic studies showed that, in contrast to classical Pd0−PdII−PdIV−PdII−Pd0 catalytic cycle, this radical cascades performed via a Pd0−PdII−PdIII−PdI−Pd0 cycle.

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Research advances in palladium-catalysed intermolecular C–H annulation of aryl halides with various aromatic ring precursors

Abstract: Transition-metal-catalysed C-H functionalization has emerged as a powerful approach for the transformation of organic molecules due to its high atom- and step economy. Among them, palladium-catalysed intermolecular C-H annulation of...

Cited by 11 publications

References 113 publications

Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C–H Activation

Versatile Tetrasilane for Time-Controlled Palladium-Catalyzed Divergent Synthesis of Silacycles via C–H Activation

Pd(II)-Catalyzed Synthesis of Polycyclic Heteroarenes via an Aminopalladation/C–H Activation/Dealkylation/Decarboxylative Cyclization Cascade

Pd/Cu Co‐Catalyzed ortho‐Arylation of Aryl Iodides via Radical Intermediates with Aryl Diazonium Salts

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