Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII/PV Hybrid Ylides DOI
Zhaofeng Wang, Xingchen Ye

Synlett, Journal Year: 2023, Volume and Issue: 35(10), P. 1153 - 1159

Published: Oct. 2, 2023

Abstract We report a novel and efficient method for oxazole synthesis through copper-catalyzed [3+2] annulation/olefination cascade between readily available iodonium–phosphonium hybrid ylides amides. An unprecedented α-phosphonium Cu carbenoid acts as the key intermediate. This features excellent regioselectivity with mild reaction conditions broad substrate scope. Its synthetic utility is demonstrated by its application in late-stage functionalizations rapid of chiral ligand based on an motif.

Language: Английский

Rhodium(III)-Catalyzed C–H Activation/[5 + 2] Cascade Annulation of Aroyl Hydrazides with Iodonium Ylides for the Synthesis of Seven-Membered Dibenzodiazepinediones DOI
He Li, Tao Chen,

Zhiwei Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

A novel Rh(III)-catalyzed C-H activation/[5 + 2] cascade annulation of aroyl hydrazides with iodonium ylides is accomplished, in which diverse seven-membered dibenzodiazepinediones were afforded moderate to excellent yields. This reaction features an ideal functional group tolerance and a wide substrate scope. Large-scale derivatization reactions conducted demonstrate the potential utility this transformation.

Language: Английский

Citations

2
Base-Mediated Visible-Light-Driven C–H Arylation of Quinoxalin-2(1H)-Ones in Ethanol DOI
Y. Pan,

Luohe Wang,

Yunhong Shi

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(19), P. 14217 - 14227

Published: Sept. 26, 2024

Prior methods for visible-light-driven C-H arylation of quinoxalin-2(1

Language: Английский

Citations

1
Hypervalent iodine-mediated formation of S–S, C–S, C–O, and C–N bonds DOI

Yu-Tsen Kuo,

Te-Jung Chai,

Cheng‐Kun Lin

et al.

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(11), P. 795 - 807

Published: April 6, 2023

Di(4-nitrobenzoyloxy)iodo]benzene (1), a hypervalent iodine compound, is easy to prepare and stable as solid, was shown be useful functional group transforming agent in this report. Oxidative synthesis of symmetrical disulfides from thiols the presence compound 1 alone performed 58–100% yields. Furthermore, ESI-MS demonstrated that premixing Ph3P yields corresponding acyloxyphosphonium, which can acylate produce thioesters 69–100% With assistance mixture Ph3P, hydroxy amino groups were benzoylated esters amides, respectively, also 9–100%

Language: Английский

Citations

3
Efficient synthesis of spirooxazine-pyrans via rhodium-catalyzed [3+3] cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones DOI

Junwei Huang,

Xuelin Yue,

Yijie Gao

et al.

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(30), P. 14430 - 14435

Published: Jan. 1, 2023

A redox-neutral access to spirooxazine-pyrans has been realized via Rh( iii )-catalysed [3+3] cascade spirocyclization of benzo[ b ][1,4]oxazines and 1-diazonaphthalen-2(1 H )-ones under extremely mild reaction conditions.

Language: Английский

Citations

3
Synthesis of 2,4-Disubstituted Oxazoles by a Copper-Catalyzed [3+2] Annulation/Olefination Cascade between Amides and IIII/PV Hybrid Ylides DOI
Zhaofeng Wang, Xingchen Ye

Synlett, Journal Year: 2023, Volume and Issue: 35(10), P. 1153 - 1159

Published: Oct. 2, 2023

Abstract We report a novel and efficient method for oxazole synthesis through copper-catalyzed [3+2] annulation/olefination cascade between readily available iodonium–phosphonium hybrid ylides amides. An unprecedented α-phosphonium Cu carbenoid acts as the key intermediate. This features excellent regioselectivity with mild reaction conditions broad substrate scope. Its synthetic utility is demonstrated by its application in late-stage functionalizations rapid of chiral ligand based on an motif.

Language: Английский

Citations

3