Rhodium‐Catalyzed C−H Activation/Annulation of N‐Aryl‐pyrazolidinones with Vinylene Carbonate DOI
Gao Huang, Jin‐Tao Yu, Changduo Pan

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(19)

Published: April 21, 2022

Abstract A rhodium‐catalyzed C−H activation/annulation of N ‐aryl‐pyrazolidinones with vinylene carbonate was developed. The utilization as the acetylene surrogate furnished successful construction non‐substituted 5,6‐pyrazolo[1,2‐ a ]cinnoline derivatives, which are difficult to synthesize through other procedures. In this work, series variously substituted pyrazolo[1,2‐ ]cinnolines were obtained in yields up 98 % broad substrate scope and excellent selectivity. Moreover, external oxidants not required protocol H 2 O CO clean by‐products.

Language: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

63

Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones DOI
Leiqing Fu, Jie‐Ping Wan

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

Citations

28

Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones DOI

Demao Chen,

Changfeng Wan, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4833 - 4838

Published: March 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Language: Английский

Citations

23

Synthesis of homophthalimide spironaphthalenones through [5 + 1] spiroannulation of aryl/alkenyl enaminones with diazo homophthalimides DOI

Chun Xia Yang,

Xinying Zhang, Xuesen Fan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4282 - 4288

Published: Jan. 1, 2023

Presented herein is a novel synthesis of homophthalimide spironaphthalenones from the cascade reaction enaminones with diazo homophthalimides.

Language: Английский

Citations

20

Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones DOI

Mingshuai Zhang,

Longkun Chen,

Zhuoyuan Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5660 - 5666

Published: Jan. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Language: Английский

Citations

20

Catalytic C H activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones DOI

Qiuyun Li,

Yannan Zhu, Yining Wang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109494 - 109494

Published: Jan. 6, 2024

Language: Английский

Citations

7

Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes DOI
Xiao Liu, Bingxin Zhou, Kelu Yan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1744 - 1750

Published: Feb. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Language: Английский

Citations

6

Rh(iii)-catalyzed C–H/C–C bond annulation of enaminones with iodonium ylides to form isocoumarins DOI
Zi Yang,

Chaoshui Liu,

Jieni Lei

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(97), P. 13483 - 13486

Published: Jan. 1, 2022

A straightforward approach to synthesise isocoumarins via Rh(III)-catalyzed C-H/C-C bond activation/annulation cascade of enaminones and iodonium ylides has been explored. The established protocol is characterized by an exceedingly simple reaction system, high regioselectivity good functional group tolerance. Moreover, this strategy may provide a new route cleavage the C(sp2)-C(O) unstrained ketones.

Language: Английский

Citations

24

Rhodium‐Catalyzed Dual C−H Activation for Regioselective Triple Annulation of Enaminones: Access to Polycyclic Naphthopyran Derivatives DOI

V. Suresh,

Muniganti Naveen Kumar,

Attunuri Nagireddy

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(11), P. 1770 - 1776

Published: March 21, 2023

Abstract Rh‐catalyzed C−H activation of arenes for oxidative annulations with alkynes stands out as a protocol polycyclic scaffolds. This perspective drives us to disclose herein rhodium catalyzed regioselective triple annulation enaminones hydroxyl‐alkynoates via double functionalization naphtho‐pyran Secondary coordination OH in alkynoate dictated the regioselectivity. Initial lactonization occurred chemoselectively on enamine part carbo rhodation followed by reductive elimination. was scalable and has shown high functionality tolerance. KIE studies were done get insight mechanism, some downstream transformations achieved show synthetic potential method.

Language: Английский

Citations

16

Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Language: Английский

Citations

16