Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

Holman, Karli R.; Stanko, Allison M; Reisman, Sarah E.

doi:10.1039/d0cs01385d

Cited by 84 publications

(32 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…On the other hand, isocyanides have been well-recognized as practical and diverse C1 synthons because of their rapid incorporation of nitrogeneous fragments in a wide variety of products . As we all know, the rapid development of palladium catalysis has tremendously increased the versatility of isocyanides-based transformation . As part of our research interests in the controllable synthesis of naphthalene condensed heterocyclic compounds, we question whether a palladium-catalyzed reaction between 8-halo-1-naphthylamines and isocyanides could be achieved (Scheme d).…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

Zhang

Liu

et al. 2022

J. Org. Chem.

View full text Add to dashboard Cite

Here, we report a novel and facile protocol for the synthesis of benz[c,d]indol-2-imines via palladium-catalyzed C–C and C–N coupling of 8-halo-1-naphthylamines with isocyanides in a single step. The reaction features broad substrate scopes and mild conditions, providing an efficient alternative for the construction of antiproliferative agents and BET bromodomain inhibitors. If 0.1 mL of H2O was added to this reaction, the N-substituted amino-1-naphthylamides could be obtained easily.

show abstract

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

Zhang

Liu

et al. 2022

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Their conspicuous practicability has been rationalized by the fact that several transformations can be carried out in one synthetic operation to cut down time and labor. Such manifested benefits of cascade reactions have become prominent in recent times for sophisticated heterocycles …”

mentioning

confidence: 99%

Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives

et al. 2022

View full text Add to dashboard Cite

Enynes have recently stimulated enormous attention toward paving the way to unique cascade cyclizations offering complex cyclic motifs from linear substrates. We describe herein a general approach to napthyridinones via the Pd-catalyzed annulation of 1,6-enynes with 2-iodoanilines. This protocol represents a rare carbo-aminative annulative cyclization via the 6-endo-trig mode, subduing the well-documented exo-trig/dig cyclizations. The regioselective aryl palladation of alkyne followed by Heck-type intramolecular coupling before isomerization were key in realizing this cascade.

show abstract

“…Accordingly, great research efforts have been made to develop efficient synthetic methods for the construction of azaheterocycle-containing molecules [4][5][6][7][8][9][10][11][12][13] . Notably, the Larock-type annulation [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] , transition metal-catalyzed cycloannulation of ambiphilic arylhalides with carbon-carbon double bonds, represents one of the most widely used and efficient methods [14][15][16][17][18][19] since the early contributions by Dieck 20 and Larock [21][22][23][24][25][26][27][28][29][30][31] . Numerous [n + 2] reactions for the synthesis of 5-, 6-membered azaheterocycles have been reported with highly reactive styrene, 1,3diene, allene, and strained cyclic alkene, in which the cyclization normally...…”

mentioning

confidence: 99%

Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes

Wang

Song

et al. 2022

Nat Commun

View full text Add to dashboard Cite

Azahetereocycles constitute important structural components in many biologically active natural compounds and marketed drugs, and represent the most promising scaffolds in drug discovery. Accordingly, the development of efficient and general synthetic methods for the construction of diverse azaheterocycles is the major goal in synthetic chemistry. Herein, we report the efficient construction of a wide range of azaheterocycles via a Pd-catalyzed migratory cycloannulation strategy with unactivated alkenes. This strategy enables the rapid synthesis of a series of 6-, 7- and 8-membered azaheterocycles in high efficiency, and features a broad substrate scope, excellent functional group tolerance under redox-neutral conditions. The significance of this finding is demonstrated by the efficient synthesis of drug-like molecules with high step-economy. Preliminary mechanistic investigations reveal that this reaction underwent a sequentially migratory insertion to alkenes, metal migration process, and the aza-Michael addition to a quinone methide intermediate.

show abstract

Palladium-catalyzed cascade cyclizations involving C–C and C–X bond formation: strategic applications in natural product synthesis

Abstract: This tutorial review highlights the use of palladium-catalyzed cascade cyclizations in natural product synthesis, focusing on cascades that construct multiple rings and form both C–C and C–X (X = O, N) bonds in a single synthetic operation.

Cited by 84 publications

References 51 publications

Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides

Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives

Construction of azaheterocycles via Pd-catalyzed migratory cycloannulation reaction of unactivated alkenes

Contact Info

Product

Resources

About