Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[<i>d</i>]oxazoles

Zhang, Pingshun; Pan, Shanfei; Chen, Wanzhi; Liu, Miaochang; Wu, Huayue

doi:10.1021/acs.joc.7b03055

Cited by 17 publications

(3 citation statements)

References 30 publications

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“…For example, ipso cyanation of ortho -substituted aryl iodides was achieved by Chen using CuCN as the cyanide source ( 145a ). Other transformations like Sonogashira coupling ( 145b ) and direct heteroarylation ( 145c ) have also been realized with the ortho acylation chemistry.…”

Section: Catalytic Reactionsmentioning

confidence: 99%

Palladium/Norbornene Cooperative Catalysis

2019

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Palladium/norbornene cooperative catalysis has emerged as a distinct approach to construct polyfunctionalized arenes from readily available starting materials. This Review provides a comprehensive overview of this field, including the early stoichiometric investigations, catalytic reaction developments, as well as the applications in the syntheses of bioactive compounds and polymers. The section of catalytic reactions is divided into two parts according to the reaction initiation mode: Pd(0)-initiated reactions and Pd(II)-initiated reactions.

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Section: Catalytic Reactionsmentioning

confidence: 99%

Palladium/Norbornene Cooperative Catalysis

2019

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“…Herein, the dichotomy of the Pd-catalyzed reactions of five-membered heteroarenes and NBD is applied to the synthesis of diheteroaryl NBEs . When the formation of the palladacycle was slow and C–H metalation of partner heteroarenes was fast, the Pd–NBD adduct underwent direct C–H heteroarylation (Figure B).…”

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confidence: 99%

Divergent Strategies for the π-Extension of Heteroaryl Halides Using Norbornadiene as an Acetylene Synthon

Jeong

Kim

et al. 2020

Org. Lett.

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Pd-catalyzed multicomponent coupling reactions of five-membered heteroaryl halides and norbornadiene (NBD) were developed. Either direct addition of (benzo)azoles or 2:1 annulation was achieved depending on the propensity of the intermediate complex to undergo palladacycle formation, determined by the nature and substitution pattern of the heteroarene. The obtained exo- and cis-diheteroaryl norbornenes underwent epimerization and retro-Diels–Alder reactions to afford the corresponding trans-isomers and π-extended heteroaromatic systems, respectively, demonstrating the versatility of NBD as an acetylene synthon.

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“…Later on, Li reported the ortho acylation/ ipso Sonogashira coupling reaction ( 101 ), [ 105 ] which could be widely used for the synthesis of important intermediates for functional materials. The ortho acylation/ ipso heteroarylation ( 102 ) [ 106 ] was also achieved in an orderly manner under the catalysis of Pd/NBE by the Chen and Wu groups, in which CuBr was essential to significantly increase the yield of the reaction. Similar to the ortho amination reaction, the large bite‐angle bidentate phosphine ligand with a flexible backbone was suitable for the ortho acylation/ ipso Heck coupling with aryl bromides as substrates.…”

Section: Typical Catellani Reactionsmentioning

confidence: 99%

Catellani Reaction: An Enabling Technology for Vicinal Functionalization of Aryl Halides by Palladium(0)/Norbornene Cooperative Catalysis

Dong

Luan

2021

Chin. J. Chem.

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The Catellani reaction, originally discovered by Catellani in 1997, and further developed by Catellani, Lautens and others, has emerged as a powerful strategy for the synthesis of polysubstituted arenes, which would be difficult to access via traditional methods. In this process, both ortho-and ipso-positions of aryl halides could be functionalized simultaneously with different electrophiles and terminating agents under the cooperative catalysis of palladium and norbornene (NBE). This review focuses on the significant progress of such transformations, and the section of typical Catellani reactions is divided into five parts according to the functionalization mode of ortho-C-H bond: alkylation, arylation, amination, acylation or thiolation.

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Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[d]oxazoles

Cited by 17 publications

References 30 publications

Palladium/Norbornene Cooperative Catalysis

Palladium/Norbornene Cooperative Catalysis

Divergent Strategies for the π-Extension of Heteroaryl Halides Using Norbornadiene as an Acetylene Synthon

Catellani Reaction: An Enabling Technology for Vicinal Functionalization of Aryl Halides by Palladium(0)/Norbornene Cooperative Catalysis

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