Condition-Controlled Selective Synthesis of Pyranone-Tethered Indazoles or Carbazoles through the Cascade Reactions of N-Nitrosoanilines with Iodonium Ylides DOI
Kelin Wang,

Xia Song,

Yongdi Xin

и другие.

Organic Letters, Год журнала: 2023, Номер 25(24), С. 4422 - 4428

Опубликована: Июнь 8, 2023

Presented herein is a condition-controlled selective synthesis of pyranone-tethered indazoles or carbazole derivatives via the cascade reactions N-nitrosoanilines with iodonium ylides. Mechanistically, formation former involves an unprecedented process including nitroso group-directed C(sp2)–H bond alkylation N-nitrosoaniline ylide followed by intramolecular C-nucleophilic addition to moiety, solvent-assisted cyclohexanedione ring opening, and transesterification/annulation. On contrary, latter initial annulation denitrosation. These developed protocols feature easily controllable selectivity, mild reaction conditions, clean sustainable oxidant (air), valuable products that are structurally diverse. In addition, utility was showcased their facile diverse transformations into synthetically biologically interesting compounds.

Язык: Английский

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C–H Bonds Elaboration DOI Creative Commons
Luca Capaldo, Davide Ravelli, Maurizio Fagnoni

и другие.

Chemical Reviews, Год журнала: 2021, Номер 122(2), С. 1875 - 1924

Опубликована: Авг. 6, 2021

Direct photocatalyzed hydrogen atom transfer (d-HAT) can be considered a method of choice for the elaboration aliphatic C–H bonds. In this manifold, photocatalyst (PCHAT) exploits energy photon to trigger homolytic cleavage such bonds in organic compounds. Selective bond may achieved by judicious abstractor (key parameters are electronic character and molecular structure), as well reaction additives. Different classes PCsHAT available, including aromatic ketones, xanthene dyes (Eosin Y), polyoxometalates, uranyl salts, metal-oxo porphyrin tris(amino)cyclopropenium radical dication. The processes (mainly C–C formation) most cases carried out under mild conditions with help visible light. aim review is offer comprehensive survey synthetic applications d-HAT.

Язык: Английский

Процитировано

833

Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)–H Bonds DOI
Bin Liu, Andrew M. Romine, Camille Rubel

и другие.

Chemical Reviews, Год журнала: 2021, Номер 121(24), С. 14957 - 15074

Опубликована: Окт. 29, 2021

Transition-metal-catalyzed, coordination-assisted C(sp3)–H functionalization has revolutionized synthetic planning over the past few decades as use of these directing groups allowed for increased access to many strategic positions in organic molecules. Nonetheless, several challenges remain preeminent, such requirement high temperatures, difficulty removing or converting groups, and, although metals provide some reactivity, employing outside palladium. This review aims give a comprehensive overview coordination-assisted, transition-metal-catalyzed, direct nonactivated bonds by covering literature since 2004 order demonstrate current state-of-the-art methods well limitations. For clarity, this been divided into nine sections transition metal catalyst with subdivisions type bond formation. Synthetic applications and reaction mechanism are discussed where appropriate.

Язык: Английский

Процитировано

373

Strategic evolution in transition metal-catalyzed directed C–H bond activation and future directions DOI
Supriya Rej, Amrita Das, Naoto Chatani

и другие.

Coordination Chemistry Reviews, Год журнала: 2020, Номер 431, С. 213683 - 213683

Опубликована: Дек. 9, 2020

Язык: Английский

Процитировано

227

Trends in the Usage of Bidentate Phosphines as Ligands in Nickel Catalysis DOI

Andrew L. Clevenger,

Ryan M. Stolley,

Justis Aderibigbe

и другие.

Chemical Reviews, Год журнала: 2020, Номер 120(13), С. 6124 - 6196

Опубликована: Июнь 3, 2020

A critically important process in catalysis is the formation of an active catalyst from combination a metal precursor and ligand, as efficacy this reaction governs amount catalyst. This Review comprehensive overview reactions catalyzed by nickel added bidentate phosphine, focusing on steps transforming precatalyst ligand into potential effects transformation catalysis. Reactions covered include common cross-coupling reactions, such Suzuki, Heck, Kumada, Negishi couplings, addition cycloadditions, C–H functionalizations, polymerizations, hydrogenations, reductive among others. Overall, most widely used with free phosphines Ni(cod)2, which accounts for ∼50% reports surveyed, distantly followed Ni(acac)2 Ni(OAc)2, account ∼10% each. By compiling these we have calculated statistics usage each Ni(cod)2 other sources. The are simple, relatively inexpensive ligands, DPPE, DCPE, DPPP, DPPB, along others more complex backbones, DPPF Xantphos. use expensive chiral scattered, but ligands BINAP, Me-Duphos, Josiphos, related analogs.

Язык: Английский

Процитировано

197

3d metallaelectrocatalysis for resource economical syntheses DOI Creative Commons
Parthasarathy Gandeepan, Lars H. Finger, Tjark H. Meyer

и другие.

Chemical Society Reviews, Год журнала: 2020, Номер 49(13), С. 4254 - 4272

Опубликована: Янв. 1, 2020

This review summarizes key developments in 3d metallaelectrocatalysis the context of resource economy molecular syntheses.

Язык: Английский

Процитировано

187

Temporary or removable directing groups enable activation of unstrained C–C bonds DOI
Ying Xia, Guangbin Dong

Nature Reviews Chemistry, Год журнала: 2020, Номер 4(11), С. 600 - 614

Опубликована: Сен. 21, 2020

Язык: Английский

Процитировано

173

Cp*Co(III)/MPAA-Catalyzed Enantioselective Amidation of Ferrocenes Directed by Thioamides under Mild Conditions DOI
Yanhua Liu, Pengxiang Li, Qi‐Jun Yao

и другие.

Organic Letters, Год журнала: 2019, Номер 21(6), С. 1895 - 1899

Опубликована: Март 6, 2019

Cp*Cobalt(III)-catalyzed enantioselective C-H amidation of ferrocenes using monoprotected amino acids (MPAAs) as chiral ligands was developed. The reaction performed under mild conditions in high yields (up to 97%) with moderate enantioselectivity 77.5:22.5 er), providing a promising strategy create planar chirality via base-metal-catalyzed activation.

Язык: Английский

Процитировано

169

Iron- and cobalt-catalyzed C(sp3)–H bond functionalization reactions and their application in organic synthesis DOI
Yungen Liu,

Tingjie You,

Hai‐Xu Wang

и другие.

Chemical Society Reviews, Год журнала: 2020, Номер 49(15), С. 5310 - 5358

Опубликована: Янв. 1, 2020

This review highlights the developments in iron and cobalt catalyzed C(sp3)–H bond functionalization reactions with emphasis on their applications organic synthesis, i.e. natural products pharmaceuticals synthesis and/or modification.

Язык: Английский

Процитировано

164

Recent advances in chelation-assisted site- and stereoselective alkenyl C–H functionalization DOI
Jian Zhang, Xiunan Lu,

Cong Shen

и другие.

Chemical Society Reviews, Год журнала: 2021, Номер 50(5), С. 3263 - 3314

Опубликована: Янв. 1, 2021

Olefinic C-H functionalization represents an atom- and step economic approach to valuable olefin derivatives from simpler ones, but controlling the selectivity remains a challenge. Remarkable progress has been made in site-selective of arenes alkanes, there are still limited examples selective olefins presumably due lability easy decomposition alkenyl moiety. Chelation-assisted activation efficient protocol for site- stereo-selective construction carbon-carbon carbon-heteroatom bonds. This review highlights recent advances vicinal- geminal-group-directed olefinic functionalization, including alkenylation, arylation, alkynylation, alkylation, halogenation, silylation, cyanation annulation by formation exo-/endo-metallocycles. In particular, is covered first time, as well distal-selective under palladium/norbornene cooperative catalysis, which provides novel disconnections retrosynthetic analysis future trend green chemistry.

Язык: Английский

Процитировано

147

Chelation-Assisted Nickel-Catalyzed C−H Functionalizations DOI
Shrikant M. Khake, Naoto Chatani

Trends in Chemistry, Год журнала: 2019, Номер 1(5), С. 524 - 539

Опубликована: Июль 8, 2019

Язык: Английский

Процитировано

134