Rhodium(III)-Catalyzed Chemo-divergent Couplings of Sulfoxonium Ylides with Oxa/azabicyclic Olefins DOI
Peiyuan Wang, Youwei Xu, Jiaqiong Sun

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(20), P. 8459 - 8463

Published: Oct. 7, 2019

Rh(III)-catalyzed C–H functionalization of sulfoxonium ylides has been realized in chemo-divergent couplings with oxa/azabicyclic olefins. Divergent [4 + 2] annulation and alkylation have attained under controlled condition. In the system, ylide functions as a traceless oxidizing directing group. contrast, introduction PivOH shunted selectivity to ring-retentive alkylation.

Language: Английский

Thioether-Directed C4-Selective C–H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides DOI

Chandrababu Naidu Kona,

Yuji Nishii, Masahiro Miura

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(12), P. 4806 - 4811

Published: June 1, 2020

Site-selective direct functionalization of an indole benzenoid core has been a great challenge due to its inherently poor reactivity. We herein demonstrate iridium-catalyzed C4-selective acylmethylation indoles using α-carbonyl sulfoxonium ylides as carbene precursors. This method exhibits high efficiency and broad functional group compatibility. The directing was easily removed or converted other functionalities after the catalysis. potential synthetic utility coupling products highlighted by constructing medium-sized polycyclic indoles.

Language: Английский

Citations

59
Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles DOI
Zhidong Jiang, Jianhui Zhou, Haoran Zhu

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(11), P. 4406 - 4410

Published: May 21, 2021

A novel Rh(III)-catalyzed C–H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a [5 + 1] cyclization product good excellent yields (up 95%), accompanied by the thorough removal acetyl and N,N-dimethyl groups two substrates from target products, rather than normally expected [4 2] products.

Language: Английский

Citations

50
Rh(iii)-catalyzed C–H annulation of sulfoxonium ylides with iodonium ylides towards isocoumarins DOI
Chuanliu Yin, Lianghao Li, Chuanming Yu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(5), P. 1112 - 1116

Published: Jan. 1, 2022

The direct synthesis of isocoumarin skeletons has been realized through the Rh( iii )-catalyzed [3 + 3] annulation sulfoxonium ylides and iodonium under mild conditions.

Language: Английский

Citations

33
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
Rhodium(III)-Catalyzed Chemo-divergent Couplings of Sulfoxonium Ylides with Oxa/azabicyclic Olefins DOI
Peiyuan Wang, Youwei Xu, Jiaqiong Sun

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(20), P. 8459 - 8463

Published: Oct. 7, 2019

Rh(III)-catalyzed C–H functionalization of sulfoxonium ylides has been realized in chemo-divergent couplings with oxa/azabicyclic olefins. Divergent [4 + 2] annulation and alkylation have attained under controlled condition. In the system, ylide functions as a traceless oxidizing directing group. contrast, introduction PivOH shunted selectivity to ring-retentive alkylation.

Language: Английский

Citations

53