Enaminones as Synthons for a Directed C−H Functionalization: RhIII‐Catalyzed Synthesis of Naphthalenes DOI

Shuguang Zhou,

Jinhu Wang, Lili Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2016, Volume and Issue: 55(32), P. 9384 - 9388

Published: June 15, 2016

The use of enaminones as effective synthons for a directed C-H functionalization is reported. Proof-of-concept protocols have been developed the Rh(III) -catalyzed synthesis naphthalenes, based on coupling with either alkynes or α-diazo-β-ketoesters. Two inherently reactive functionalities (hydroxy and aldehyde groups) are integrated into newly formed cyclic framework broad range substituents tolerated, rendering target products readily available further elaboration.

Language: Английский

Cobalt(III)‐Catalyzed Redox‐Neutral Synthesis of Unprotected Indoles Featuring an N−N Bond Cleavage DOI

Andreas Lerchen,

Suhelen Vásquez‐Céspedes,

Frank Glorius

et al.

Angewandte Chemie International Edition, Journal Year: 2016, Volume and Issue: 55(9), P. 3208 - 3211

Published: Feb. 2, 2016

Abstract A redox‐neutral cobalt(III)‐catalyzed synthetic approach for the direct synthesis of unprotected indoles showcasing an N−N bond cleavage is reported. The herein newly introduced Boc‐protected hydrazines establish a beneficial addition to limited portfolio oxidizing directing groups cobalt(III) catalysis. Moreover, developed catalytic methodology tolerates good variety functional groups.

Language: Английский

Citations

175
Redox‐Neutral Manganese(I)‐Catalyzed C−H Activation: Traceless Directing Group Enabled Regioselective Annulation DOI
Qingquan Lu,

Steffen Greßies,

Sara Cembellín

et al.

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(41), P. 12778 - 12782

Published: Aug. 15, 2017

Abstract A strategy is reported in which traceless directing groups (TDGs) are used to promote the redox‐neutral Mn I ‐catalyzed regioselective synthesis of N‐heterocycles. Alkyne coupling partners bearing a group, serves as both chelator and internal oxidant, were control regioselectivity annulation reactions. This operationally simple approach highly effective with previously challenging unsymmetrical alkyne systems, including unbiased dialkyl alkynes, perfect regioselectivity. The conditions ability carry out on gram scale underscore usefulness this method. application concise bioactive compound PK11209 pharmaceutical moxaverine also described.

Language: Английский

Citations

173
Synthesis of hydroxylamine from air and water via a plasma-electrochemical cascade pathway DOI
Xiangdong Kong, Jie Ni, Zhimin Song

et al.

Nature Sustainability, Journal Year: 2024, Volume and Issue: 7(5), P. 652 - 660

Published: April 19, 2024

Language: Английский

Citations

23
Internal Oxidant‐Triggered Aerobic Oxygenation and Cyclization of Indoles under Copper Catalysis DOI
Huawen Huang, Jinhui Cai, Xiaochen Ji

et al.

Angewandte Chemie International Edition, Journal Year: 2015, Volume and Issue: 55(1), P. 307 - 311

Published: Oct. 20, 2015

Abstract A concise synthesis of pyrazolo[1,5‐a]indole derivatives by copper‐catalyzed aerobic oxygenation and cyclization indoles with oxime acetates is described. This protocol represents an elegant example N‐1, C‐2, C‐3 tri‐functionalization in one‐pot. Mechanistic studies indicate the reaction proceeds through a radical procedure. Oximes as internal oxidant have been demonstrated to be driver initiate oxidation, which provides new oxidative pattern for C‐H functionalization even high atom‐ step‐economy.

Language: Английский

Citations

173
Enaminones as Synthons for a Directed C−H Functionalization: RhIII‐Catalyzed Synthesis of Naphthalenes DOI

Shuguang Zhou,

Jinhu Wang, Lili Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2016, Volume and Issue: 55(32), P. 9384 - 9388

Published: June 15, 2016

The use of enaminones as effective synthons for a directed C-H functionalization is reported. Proof-of-concept protocols have been developed the Rh(III) -catalyzed synthesis naphthalenes, based on coupling with either alkynes or α-diazo-β-ketoesters. Two inherently reactive functionalities (hydroxy and aldehyde groups) are integrated into newly formed cyclic framework broad range substituents tolerated, rendering target products readily available further elaboration.

Language: Английский

Citations

166