Three-Component Synthesis of Isoquinolone Derivatives via Rh(III)-Catalyzed C-H Activation and Tandem Annulation.

A one-pot three-component synthesis of multifunctionalized isoquinolones from 2-oxazolines, iodonium ylides, and carboxylic acids via Rh(III)-catalyzed oxazolinyl-directed C-H activation and tandem annulation under redox-neutral conditions has been developed. This catalytic system is characterized by readily available starting materials, a wide tolerance of functional groups, a short reaction time, and high yields. The synthetic utility of the cascade reaction was further demonstrated by a gram-scale synthesis and derivatization of the obtained products.

[1]  Jidan Liu,et al.  Three‐Component Synthesis of Benzofuran‐3(2H)‐ones with Tetrasubstituted Carbon Stereocenters via Rh(III)‐Catalyzed C‐H/C‐C Bond Activation and Cascade Annulation , 2022, Advanced Synthesis & Catalysis.

[2]  Yong‐Gui Zhou,et al.  Recent advances in transition-metal-catalyzed carbene insertion to C-H bonds. , 2022, Chemical Society reviews.

[3]  Chuanming Yu,et al.  Rh(III)-catalyzed C-H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins. , 2022, Organic & biomolecular chemistry.

[4]  Yang Gao,et al.  Divergent synthesis of fused N-heterocycles via rhodium-catalysed [4+2] cyclization of pyrazolidinones with iodonium ylides , 2022, Organic Chemistry Frontiers.

[5]  M. Cushman Design and Synthesis of Indenoisoquinolines Targeting Topoisomerase I and Other Biological Macromolecules for Cancer Chemotherapy. , 2021, Journal of medicinal chemistry.

[6]  Binsheng He,et al.  A facile route to pyrazolo[1,2‐a]cinnoline via Rhodium(III)‐catalysed annulation of pyrazolidinoes and iodonium ylides , 2021, Asian Journal of Organic Chemistry.

[7]  S. Sen,et al.  A sustainable C-H functionalization of indoles, pyrroles and furans under a blue LED with iodonium ylides. , 2021, Organic & biomolecular chemistry.

[8]  S. Ji,et al.  Rh(iii)-Catalyzed C(sp2)–H functionalization/cyclization cascade of N-carboxamide indole and iodonium reagents for access to indoloquinazolinone derivatives , 2021, Green Chemistry.

[9]  L. Gu,et al.  Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C-H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides. , 2021, Organic letters.

[10]  Jidan Liu,et al.  Rhodium(III)-Catalyzed Oxidative Cyclization of Oxazolines with Cyclopropanols: Synthesis of Isoindolinones. , 2021, Organic letters.

[11]  P. Ravikumar,et al.  Ruthenium-Catalyzed Regioselective C(sp2)-H Activation/Annulation of N-(7-Azaindole)amides with 1,3-Diynes Using N-Amino-7-azaindole as the N,N-Bidentate Directing Group. , 2021, The Journal of organic chemistry.

[12]  S. Nanduri,et al.  Rh(III)-Catalyzed Chemodivergent Annulations between Indoles and Iodonium Carbenes: A Rapid Access to Tricyclic and Tetracyclic N-Heterocylces. , 2021, Organic letters.

[13]  G. Hammond,et al.  Cobalt-Catalyzed C-H Activation/Annulation of Benzamides with Fluorine-Containing Alkynes: A Route to 3- and 4-Fluoroalkylated Isoquinolinones. , 2021, The Journal of organic chemistry.

[14]  Jidan Liu,et al.  Synthesis of Functionalized Diarylbenzofurans via Ru-Catalyzed C–H Activation and Cyclization under Air: Rapid Access to the Polycyclic Scaffold of Diptoindonesin G , 2021, Organic Chemistry Frontiers.

[15]  Masilamani Tamizmani,et al.  Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of N-methoxybenzamides with a Rh(III)-catalyst. , 2020, Chemical communications.

[16]  Xingwei Li,et al.  Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation. , 2020, Organic letters.

[17]  L. Qiu,et al.  Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes. , 2020, Chemical communications.

[18]  Zhao‐Qing Liu,et al.  Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles. , 2020, Chemical communications.

[19]  Shifa Zhu,et al.  Recent progress on donor and donor-donor carbenes. , 2020, Chemical Society reviews.

[20]  Yi Dong,et al.  Cp*RhIII-Catalyzed Sulfonamide-Directed Ortho Arene C-H Carbenoid Functionalization with Pyridotriazoles. , 2019, Organic letters.

[21]  Zhi Zhou,et al.  Rh(III)-catalyzed C-H activation/cycloisomerization of N-phenoxyacetamides with enynones for one-pot assembly of furylated 2-alkenylphenols. , 2019, The Journal of organic chemistry.

[22]  Diksha Singh,et al.  Oxazolinyl-Assisted Ru(II)-Catalyzed C-H Allylation with Allyl Alcohols and Synthesis of 4-methyleneisochroman-1-ones. , 2019, The Journal of organic chemistry.

[23]  Danzhou Yang,et al.  Indenoisoquinoline Topoisomerase Inhibitors Strongly Bind and Stabilize the MYC Promoter G-Quadruplex and Downregulate MYC. , 2019, Journal of the American Chemical Society.

[24]  G. S. Kumar,et al.  Oxazolinyl‐Assisted Ru(II)‐Catalyzed C−H Functionalization Based on Carbene Migratory Insertion: A One‐Pot Three‐Component Cascade Cyclization , 2018, Advanced Synthesis & Catalysis.

[25]  Xiuling Cui,et al.  Rhodium(III)‐Catalyzed Synthesis of N ‐(2‐Acetoxyalkyl)isoquinolones from Oxazolines and Alkynes through C−N Bond Formation and Ring‐Opening , 2018, Advanced Synthesis & Catalysis.

[26]  W. Zeng,et al.  Ru (II)-Catalyzed Coupling-Cyclization of Sulfoximines with alpha -Carbonyl Sulfoxonium Ylides as an Approach to 1,2-Benzothiazines , 2018, Advanced Synthesis & Catalysis.

[27]  G. Zheng,et al.  Rhodium(iii)-catalyzed chemodivergent annulations between N-methoxybenzamides and sulfoxonium ylides via C-H activation. , 2018, Chemical communications.

[28]  Annette Bayer,et al.  Rhodium-Catalyzed Synthesis of Sulfur Ylides via in Situ Generated Iodonium Ylides. , 2017, Organic letters.

[29]  J. Wang,et al.  Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion. , 2017, Chemical reviews.

[30]  C. Janot,et al.  Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C-H Bonds. , 2017, Angewandte Chemie.

[31]  G. Zheng,et al.  Sulfoxonium Ylides as a Carbene Precursor in Rh(III)-Catalyzed C-H Acylmethylation of Arenes. , 2017, Organic letters.

[32]  N. Chatani,et al.  Nickel-catalyzed C–H/N–H annulation of aromatic amides with alkynes in the absence of a specific chelation system† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01750b Click here for additional data file. , 2017, Chemical science.

[33]  L. Ackermann,et al.  Iron-catalyzed C-H/N-H activation by triazole guidance: versatile alkyne annulation. , 2017, Chemical communications.

[34]  Sukbok Chang,et al.  [4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand. , 2017, Angewandte Chemie.

[35]  S. Ma,et al.  New Approaches to the Synthesis of Metal Carbenes. , 2016, Angewandte Chemie.

[36]  Akira Yoshimura,et al.  Advances in Synthetic Applications of Hypervalent Iodine Compounds. , 2016, Chemical reviews.

[37]  F. Glorius,et al.  Rh(III) -Catalyzed C-H Activation with Pyridotriazoles: Direct Access to Fluorophores for Metal-Ion Detection. , 2015, Angewandte Chemie.

[38]  A. Maguire,et al.  Modern Organic Synthesis with α-Diazocarbonyl Compounds. , 2015, Chemical reviews.

[39]  O. Daugulis,et al.  Cobalt-catalyzed, aminoquinoline-directed C(sp²)-H bond alkenylation by alkynes. , 2014, Angewandte Chemie.

[40]  J. Wang,et al.  Rhodium(III)-catalyzed ortho alkenylation of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through C-H activation. , 2014, Angewandte Chemie.

[41]  Jun Zhu,et al.  A chiral cagelike copper(I) catalyst for the highly enantioselective synthesis of 1,1-cyclopropane diesters. , 2012, Angewandte Chemie.

[42]  Dan Yang,et al.  Pd-catalysed synthesis of isoquinolinones and analogues via C-H and N-H bonds double activation. , 2012, Chemical communications.

[43]  Zhenyuan Miao,et al.  New strategies in the discovery of novel non-camptothecin topoisomerase I inhibitors. , 2011, Current medicinal chemistry.

[44]  N. Chatani,et al.  Nickel-catalyzed chelation-assisted transformations involving ortho C-H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes. , 2011, Journal of the American Chemical Society.

[45]  L. Ackermann,et al.  Ruthenium-catalyzed oxidative annulation by cleavage of C-H/N-H bonds. , 2011, Angewandte Chemie.

[46]  R. Crabtree,et al.  Rh-catalyzed oxidative coupling between primary and secondary benzamides and alkynes: synthesis of polycyclic amides. , 2010, The Journal of organic chemistry.

[47]  T. Rovis,et al.  Rhodium-catalyzed oxidative cycloaddition of benzamides and alkynes via C-H/N-H activation. , 2010, Journal of the American Chemical Society.

[48]  A. Charette,et al.  General method for the synthesis of phenyliodonium ylides from malonate esters: easy access to 1,1-cyclopropane diesters. , 2009, The Journal of organic chemistry.

[49]  Toshimasa Tanaka,et al.  Discovery, synthesis and biological evaluation of isoquinolones as novel and highly selective JNK inhibitors (2). , 2008, Bioorganic & medicinal chemistry.

[50]  T. Okada,et al.  Rhodium(II)-catalyzed transylidation of aryliodonium ylides: electronic effects of aryl groups determine their thermodynamic stabilities. , 2008, Organic letters.

[51]  P. Müller Asymmetric transfer of carbenes with phenyliodonium ylides. , 2004, Accounts of chemical research.

[52]  G. Kostakis,et al.  Alkenyl C-H insertion of iodonium ylides into pyrroles: studies toward the total syntheses of tolmetin and amtolmetin guacil. , 2003, Organic letters.

[53]  P. Müller,et al.  Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides. † , 2000, Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry.