Rhodium(III)‐Catalyzed Dehydrogenative Annulation of 2‐Arylindazoles with Cyclic Enones

Devulapally, Yogananda Chary; Ittamalla, Chaitanya; Sridhar, Balasubramanian; Reddy, Basireddy Venkata Subba

doi:10.1002/ejoc.202100272

Cited by 9 publications

(1 citation statement)

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“…66 Moreover, indazole and pyrazolo In 2021, Reddy and co-workers developed a rhodium(III)catalyzed oxidative dehydrogenative annulation of 2-aryl-2Hindazoles with cyclic enones in the presence of Cu(OAc) 2 . 67 A series of 3,4-dihydroindazolo[2,3-f ] phenanthridin-1(2H)-ones were obtained in good yields with high selectivity. However, when AgSbF 6 was utilized instead of Cu(OAc) 2 , the corresponding uncyclized 3-(2-(2H-indazol-2-yl)phenyl)cyclohexan-1ones were produced exclusively (Scheme 43).…”

Section: Reviewmentioning

confidence: 99%

Recent advances in C–H functionalization of 2H-indazoles

Yang

Pan

2022

Org. Biomol. Chem.

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Section: Reviewmentioning

confidence: 99%

Recent advances in C–H functionalization of 2H-indazoles

Yang

Pan

2022

Org. Biomol. Chem.

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Rhodium‐Catalyzed CH Functionalization to Construct Annulated Molecules

Mahato

Sarkar

Naskar

et al. 2022

Handbook of CH-Functionalization

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Rhodium complexes are exceptionally significant in homogeneous catalysis. The synthetic community observed the rapid burgeoning of such rhodium catalysis since the discovery of Wilkinson's catalyst. Rhodium‐catalyzed tandem C(sp 2 )H/C(sp 3 )H activation and annulation with alkenes, alkynes, arenes, and other reactive partners is a rapidly growing research field to obtain a new class of heterocycles and thereby generates potential biologically active pharmacophores. Superior reactivity of rhodium catalysts is attributed due to its good π‐acceptor character that favors the CH bond activation reaction of substrates containing a wide range of directing groups, such as amides, imines, carboxylic acid (derivatives), benzylic alcohols, ketones, various heterocycles and shown efficiency toward annulation reaction with various befitting partners; even undirected CH activations have also been achieved. This article provides a brief account of the recent developments in rhodium‐catalyzed CH activation/annulation reactions for the synthesis of new classes of fused cyclic scaffolds using suitable coupling partners. For the rhodium‐catalyzed annulation strategies, different types of cyclization reactions, namely, oxidative, redox‐neutral, photoredox, electrochemical reactions are discussed. In addition, the enantioselective synthesis of annulated molecules using chiral rhodium catalysts has also been highlighted.

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Rh(III)‐Catalyzed Oxidative Annulation of 2‐Aryl‐1H‐benzo[d]imidazoles with 1,4‐Quinones through C−H Activation

2022

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Rh(III) catalyzed oxidative annulation of 2-aryl-1Hbenzo[d]imidazoles with 1,4-quinones has been achieved for the synthesis of a novel class of benzo[4,5]imidazo[1,2f]phenanthridine-1,4-dione frameworks through a sequential CÀ C and CÀ N bond formations in a single-step operation. This is the first report on the oxidative annulation of 2-aryl-1Hbenzo[d]imidazoles with 1,4-quinones to produce highly functionalized phenanthridine-1,4-dione derivatives.

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Rhodium(III)‐Catalyzed Dehydrogenative Annulation of 2‐Arylindazoles with Cyclic Enones

Cited by 9 publications

References 29 publications

Recent advances in C–H functionalization of 2H-indazoles

Recent advances in C–H functionalization of 2H-indazoles

Rhodium‐Catalyzed CH Functionalization to Construct Annulated Molecules

Rh(III)‐Catalyzed Oxidative Annulation of 2‐Aryl‐1H‐benzo[d]imidazoles with 1,4‐Quinones through C−H Activation

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