Synthesis of naphthalene-substituted aromatic esters via Rh(iii)-catalyzed C–H bond naphthylation and cascade directing group transformation DOI
Yue Cui, Siyu Li, Hesheng Wang

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(95), С. 13230 - 13233

Опубликована: Янв. 1, 2022

A regioselective Rh(III)-catalyzed C-H bond naphthylation and cascade directing group (DG) transformation has been realized with aryl imidates oxa bicyclic alkenes. Diverse naphthalene-substituted aromatic esters were synthesized fruitfully. The DG into ester endows the strategy chances of further functionalization derivatization. Preliminary mechanistic studies demonstrate that carbonyl oxygen possibly originates from corresponding alkene.

Язык: Английский

Rh-Catalyzed [4 + 2] Annulation with a Removable Monodentate Structure toward Iminopyranes and Pyranones by C–H Annulation DOI
Leiqing Fu, Wenqiang Xu, Maoping Pu

и другие.

Organic Letters, Год журнала: 2022, Номер 24(16), С. 3003 - 3008

Опубликована: Апрель 20, 2022

The Rh-catalyzed reactions of N-pyridinyl enaminones with internal alkynes leading to the synthesis iminopyranes via a key C–H bond activation and subsequent tautomeric O–H cleavage are reported. Moreover, pyridine ring in amino group acts as an auxiliary monodentate site for this annulation can be easily removed by simple hydrolysis afford pyranones.

Язык: Английский

Процитировано

40

Three-component synthesis ofN-naphthyl pyrazolesviaRh(iii)-catalyzed cascade pyrazole annulation and Satoh–Miura benzannulation DOI

Demao Chen,

Liyun Zhou,

Yunyun Liu

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(27), С. 4036 - 4039

Опубликована: Янв. 1, 2023

The synthesis of N-naphthyl pyrazoles has been realized by the direct three-component reactions enaminones, aryl hydrazine hydrochlorides and internal alkynes via Rh(III) catalysis. synthetic employing simple substrates lead to simultaneous construction dual cyclic moieties, including a pyrazole ring phenyl ring, sequential formation two C-N three C-C bonds.

Язык: Английский

Процитировано

33

Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones DOI

Mingshuai Zhang,

Longkun Chen,

Haifeng Sun

и другие.

Organic Letters, Год журнала: 2023, Номер 25(39), С. 7214 - 7219

Опубликована: Сен. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Язык: Английский

Процитировано

33

Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand DOI

Junya Kitano,

Yuji Nishii, Masahiro Miura

и другие.

Organic Letters, Год журнала: 2022, Номер 24(31), С. 5679 - 5683

Опубликована: Июль 28, 2022

Benzofuran is a privileged structure in many bioactive compounds; however, the controlled synthesis of C2,C3-nonsubstituted benzofurans has been scarce. In particular, cumbersome multistep processes are inevitable for most inaccessible C4-substituted isomers. Herein, we report Rh-catalyzed direct vinylene annulation readily available m-salicylic acid derivatives with carbonate to achieve selective construction benzofurans. The Weinreb amide directing group facilitated following product derivatization. reaction mechanism was investigated by DFT calculations.

Язык: Английский

Процитировано

26

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate DOI

Ayumi Inami,

Yuji Nishii, Koji Hirano

и другие.

Organic Letters, Год журнала: 2023, Номер 25(18), С. 3206 - 3209

Опубликована: Май 4, 2023

Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become promising synthetic method; however, catalytic synthesis 3,4-nonsubstituted isoquinolines by formal acetylene been scarce to date. Herein, we introduce vinyl selenone as an effective surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered diselenide recycled. product readily converted 1-aminoisoquinolines.

Язык: Английский

Процитировано

11

Rhenium-catalyzed synthetic method of 1,2-dihydroisoquinolines and isoquinolines by the intramolecular cyclization of 2-alkynylaldimines or 2-alkynylbenzylamines DOI

Rui Umeda,

Tetsuya Ishida,

Shintaro Mori

и другие.

Tetrahedron, Год журнала: 2024, Номер 154, С. 133854 - 133854

Опубликована: Фев. 2, 2024

Язык: Английский

Процитировано

4

Recent advances in rhodium-catalyzed C(sp2)–H (hetero)arylation DOI

Zixian Yang,

Jin‐Tao Yu, Changduo Pan

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(39), С. 8442 - 8465

Опубликована: Янв. 1, 2021

Recent achievements in rhodium-catalyzed arylations through C(sp 2 )–H bond activation were summarized.

Язык: Английский

Процитировано

26

Diverse reactivity of alkynes in C–H activation reactions DOI
Shyam Kumar Banjare, Pranav Shridhar Mahulkar, Tanmayee Nanda

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(74), С. 10262 - 10289

Опубликована: Янв. 1, 2022

The metal–carbon bond generated through C–H activation is a key organometallic intermediate, which could be further functionalized with various reacting partners. Among the coupling partners used in metal-catalysed activation, alkynes occupy prominent position on account of their varied reactivity.

Язык: Английский

Процитировано

18

Breaking the Trend: Insight into Unforeseen Reactivity of Alkynes in Cobalt-Catalyzed Weak Chelation-Assisted Regioselective C(4)–H Functionalization of 3-Pivaloyl Indole DOI
Shyam Kumar Banjare, Tanmayee Nanda, Bedadyuti Vedvyas Pati

и другие.

ACS Catalysis, Год журнала: 2021, Номер 11(18), С. 11579 - 11587

Опубликована: Сен. 3, 2021

Unique reactivity of diphenylacetylene has been uncovered through weak chelation-assisted cobalt-catalyzed regioselective C(4)–H activation 3-pivolyl indole. α-Hydroxy ketone and α,β-unsaturated derivatives have synthesized in good yields from indole alkynes. Notably, the C(4)–H-functionalized product was obtained with high stereo- regioselectivity simply by changing coupling partner symmetrical alkynes to unsymmetrical aromatic-aliphatic Most importantly, trifluoroethanol acts as a sole source water for this conversion. Quantitative detection bis(2,2,2-trifluoroethyl) ether dry 19F NMR LCMS studies indirectly confirms situ formation water. A six-membered cobaltacycle intermediate detected HRMS, also, further confirmed quantum mechanical calculations, which accounts highly functionalization.

Язык: Английский

Процитировано

22

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline DOI

Q. Liu,

Wenquan Wang, Meng Liu

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июль 3, 2023

Abstract Pyrrolo[1,2‐ α ]quinoxaline and its derivatives have excellent biological activity photoelectric properties, are widely used in the fields of pharmaceutical preparations organic electroluminescence. This review starts from catalysts summarizes single metal catalysis palladium, rhodium, iron, molybdenum, copper, as well synergistic iron molybdenum bimetallic metal‐free catalytic systems for synthesis pyrrolo[1,2‐ ]quinoxaline. The mechanism different was detailly introduced analysed. By analysing advantages disadvantages existing catalyst systems, prospects new methods presented.

Язык: Английский

Процитировано

7