Rh(III)-Catalyzed Tandem [4+2] Annulation To Construct Functional Dihydroisoquinolinones DOI
Lin Dong, Jiahui Yang

Synthesis, Journal Year: 2022, Volume and Issue: 54(14), P. 3271 - 3281

Published: March 3, 2022

Abstract A highly efficient Rh(III)-catalyzed tandem [4+2] annulation to construct functional dihydroisoquinolinone derivatives with an alkenyl side chain by insertion into N–O bond as internal oxidation process has been achieved. wide range of 1,3-dienes the coupling partners makes this simple methodology even more useful.

Language: Английский

Recent advances in transition metal-catalyzed heteroannulative difunctionalization of alkenes via C–H activation for the synthesis of heterocycles DOI
Jianchao Liu, Xiao Xiao, Yinlong Lai

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(8), P. 2256 - 2279

Published: Jan. 1, 2022

In this review article, we summarized recent advances in the transition metal-catalyzed heteroannulative difunctionalization of alkenes via direct C–H activation to access heterocyclic frameworks.

Language: Английский

Citations

57
Palladium/TY-Phos-Catalyzed Asymmetric Heck/Tsuji–Trost Reaction of o-Bromophenols with 1,3-Dienes DOI

Youshao Tu,

Bing Xu, Qian Wang

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(8), P. 4378 - 4383

Published: Feb. 16, 2023

2,3-Dihydrobenzofurans are crucial building blocks in the synthesis of natural products and pharmaceutical molecules. However, their asymmetric has been a long-standing formidable challenge so far. In this work, we developed highly enantioselective Pd/TY-Phos-catalyzed Heck/Tsuji-Trost reaction o-bromophenols with various 1,3-dienes, allowing expedient access to chiral substituted 2,3-dihydrobenzofurans. This features excellent regio- enantiocontrol, high functional group tolerance, easy scalability. More importantly, demonstration method as valuable tool for construction optically pure (R)-tremetone fomannoxin is highlighted.

Language: Английский

Citations

28
Coupling partner-dependent unsymmetrical C–H functionalization of N-phenoxyacetamides leading to sophisticated spirocyclic scaffolds DOI

Xia Song,

Kelin Wang,

Lian Xue

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4583 - 4590

Published: Jan. 1, 2022

In this paper, a coupling partner-dependent unsymmetrical C–H functionalization of N -phenoxyacetamides leading to the formation sophisticated spirocyclic scaffolds is presented.

Language: Английский

Citations

25
Asymmetric cascades of the π-allyl complex: a journey from transition-metal catalysis to metallaphotocatalysis DOI
Santosh K. Nanda

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(76), P. 11298 - 11319

Published: Jan. 1, 2023

The enantioselective catalytic cascade involving Tsuji-Trost allylation has provided a viable strategy for the construction of multiple asymmetric C-C and C-X centres numerous methods have been developed around it synthesis various vital scaffolds. synthetic utility this was enhanced by replacing customary allyl acetates with ethylene diacetates/dicarbonates, vinyl epoxides, oxetanes, carbonates, cyclopropanes, enynes, dienes using transition-metal catalysis. One more milestone achieved when metallaphotocatalysis necessary platform these cascades cheaper metal. This review will provide summary from 2015.

Language: Английский

Citations

10
Base-tuned selective 1,2-dichloromethylhydroxylation and 1,2-peroxyhydroxylation of 1,3-dienes via a tandem radical process DOI
Jiantao Zhang, Weiming Zhu, Peng Zhou

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(62), P. 9481 - 9484

Published: Jan. 1, 2023

A catalyst-free 1,2-difunctionalization of 1,3-dienes with CHCl3 and TBHP in the presence NEt3 to give dichloromethylhydroxylation products was developed. Various substituents on aryl ring dienes tolerated reactions gave corresponding moderate good yields. When Na2CO3 employed as base, key intermediate α-amino radical could not be formed; therefore, 1,2-peroxyhydroxylation were obtained instead. This protocol provides an effective functional group tolerant strategy for diene 1,2-difunctionalization, thus providing great potential further functionalization modification synthetic molecules.

Language: Английский

Citations

8
Half-Sandwich d6-Metal (CoIII, RhIII, IrIII, RuII)-Catalyzed Enantioselective C–H Activation DOI Creative Commons
Pu‐Fan Qian, Jun-Yi Li, Yibo Zhou

et al.

SynOpen, Journal Year: 2023, Volume and Issue: 07(04), P. 466 - 485

Published: Sept. 6, 2023

Abstract Transition-metal-catalyzed enantioselective C–H activation provides a straightforward strategy to synthesize chiral molecules from readily available sources. In this graphical review, we summarize the progress on half-sandwich d6-metal (CoIII, RhIII, IrIII, RuII)-catalyzed functionalization reactions. The review is categorized according type of metal catalyst and ligand employed. Representative enantio-determining models catalytic cycles are presented.

Language: Английский

Citations

7
Copper(I)-Catalyzed Dearomatization of Benzofurans with 2-(Chloromethyl)anilines through Radical Addition and Cyclization Cascade DOI

Chong-Yu Liu,

Zhao Jin, Cheng‐Xue Pan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 519 - 524

Published: Jan. 8, 2024

Herein, we described a copper(I)-catalyzed dearomatization of benzofurans with 2-(chloromethyl)anilines to prepare various tetrahydrobenzofuro[3,2-

Language: Английский

Citations

2
Cobalt(III)-Catalyzed Regio- and Chemoselective [4 + 2]-Annulation of N-Chlorobenzamides/Acrylamides with 1,3-Dienes at Room Temperature DOI

Balu Ramesh,

Masilamani Jeganmohan

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(9), P. 5713 - 5729

Published: April 12, 2022

Co(III)-catalyzed regio- and chemoselective redox-neutral C-H annulation of arylamides/acrylamides with 1,3-dienes is described. The present reaction was well suited a less-reactive 1,3-butadiene. By employing this protocol, pharmaceutically important 3,4-dihydroisoquinolinones were synthesized in good yields. Furthermore, the prepared converted into highly oxirane derivatives A plausible mechanistic cycle proposed supported by competition experiment kinetic isotopic effect (KIE) studies.

Language: Английский

Citations

10
Rhodium-catalyzed enantioselective annulation of N-phenoxyacetamides with 1,3-dienes DOI
Hui Yang, Ziqi Yang,

Suzhen Zhang

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(10), P. 2842 - 2846

Published: June 6, 2023

Language: Английский

Citations

6
Cobalt-Catalyzed Z to E Geometrical Isomerization of 1,3-Dienes DOI
Wei Wang, Shuying He, Yuqing Zhong

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(7), P. 4712 - 4723

Published: March 11, 2022

An efficient cobalt-catalyzed geometrical isomerization of 1,3-dienes is described. In the combination a CoCl2 precatalyst with an amido-diphosphine-oxazoline ligand, E/Z mixtures proceed in stereoconvergent manner, affording (E) isomers high stereoselectivity. This facile transformation features broad substrate scope good functional group tolerance and could be scaled up to gram scale smoothly catalyst loading 1 mol %.

Language: Английский

Citations

9