Cationic Palladium‐Catalyzed [5+2] Annulation: Synthesis of 1‐Benzoxepines from 2‐Aroylmethoxyarylboronic Acids

Liu, Guixia; Lu, Xin

doi:10.1002/adsc.200700369

Cited by 46 publications

(14 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to these results, it was presumed that the chiral catalyst interfered with the chiral substrates, resulting in different stereocontrol; ( S )‐2‐( N ‐ tert ‐butanesulfinylimino)arylboronic acid and the cationic palladium complex constituted a matched pair leading to the enhancement of diastereoselectivity. In addition, a moderate enantioselectivity of 50% ee was reported by the same authors in the domino annulation of racemic 2‐aroylmethoxyarylboronic acids with alkynes to give the corresponding 1‐benzoxepines upon catalysis with either {Pd[( S,S )‐bdpp](H 2 O) 2 } 2+ (OTf − ) 2 or [Pd( R )‐BINAP(H 2 O) 2 ] 2+ (OTf − ) 2 ] 25…”

Section: One‐ and Two‐component Domino Reactionsmentioning

confidence: 80%

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Ahn

Kim

Lee

et al. 2010

Phytotherapy Research

View full text Add to dashboard Cite

Chronic kidney disease (CKD) is a common cause of end-stage renal disease. Antihypertensive agents are used clinically to inhibit the progression of CKD, but cannot prevent eventual renal failure. This study investigated the effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, in rats suffering from CKD induced by 5/6 nephrectomy. After development of renal insufficiency, the rats were treated with Tanshinone IIA (10 mg/kg) for 8 weeks. Serum creatinine, angiotensin II (Ang II), transforming growth factor β1 (TGF-β1) and collagen IV levels were significantly reduced in Tanshinone IIA treated rats compared with a control group. In addition, Tanshinone IIA suppressed increases in urinary protein excretion in CKD rats. These findings suggest that chronic oral administration of Tanshinone IIA can improve renal dysfunction associated with CKD.

show abstract

Section: One‐ and Two‐component Domino Reactionsmentioning

confidence: 80%

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Ahn

Kim

Lee

et al. 2010

Phytotherapy Research

View full text Add to dashboard Cite

show abstract

“…26 The first step in this reaction is thought to be intramolecular palladium(II) catalyzed cyclization of the aromatic ring onto the alkyne, followed by hydroarylation of a second substrate molecule with the resulting quinolinylpalladium species. Intermolecular variants for the synthesis of oxindoles, 27 benzoxepines, 28 and thiadiazafluorenones 29 have been successful as well. An interesting variation of this chemistry was developed by Aurrecoechea and co-workers, who accessed trien-1-ols 3 by reduction of 4,5-epoxyalk-2-ynyl esters 2 with samarium iodide.…”

Section: Examples Of Synthetically Enabling Protodepalladation Reactionsmentioning

confidence: 99%

Protodepalladation as a Strategic Elementary Step in Catalysis

O’Duill

Engle

2018

Synthesis

View full text Add to dashboard Cite

Protodepalladation is the redox-neutral conversion of a C-Pd(II) bond to a C-H bond promoted by a Brønsted acid. It can be viewed as the microscopic reserves of Pd(II)-mediated C-H cleavage. In the context of catalytic reaction development, protodepalladation offers a means of converting organopalladium(II) intermediates to organic products without a change in oxidation state at the metal center. Hence, when integrated into catalytic cycles, it can be a uniquely enabling elementary step. The goal of this Review is to provide an overview of protodepalladation, including exploration of different reactions types, discussion of literature examples, and analysis of mechanistic features. Our hope is that this review will stimulate other researchers in the field to pursue new applications of this underexploited step in catalysis.

show abstract

“…In addition, a moderate enantioselectivity of 50% ee was reported by the same authors in the domino annulation of racemic 2-aroylmethoxyarylboronic acids with alkynes to give the corresponding 1-benzoxepines upon catalysis with either [Pd[(S,S)bdpp](H 2 O) 2 ]] 2+ (OTf -) 2 or [Pd(R)-BINAP(H 2 O) 2 ] 2+ ·(OTf -) 2 ]. [25] dioxane, r. Copper-catalyzed domino reactions have been used for the synthesis of carbocycles, as well as for heterocycles, such as indoles, benzoxazoles, and quinoxalines. Among these reactions, are enantioselective copper-catalyzed domino reactions initiated by conjugate additions.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

2012

View full text Add to dashboard Cite

International audienceSince the first definition of domino reactions by Tietze in 1993, an explosive number of these fascinating reactions have been developed, allowing easily building complex chiral molecular architectures from simple materials to be achieved in a single step. Even more interesting, the possibility to join two or more reactions in one asymmetric domino process catalyzed by chiral metal catalysts has rapidly become one challenging goal for chemists, due to economical advantages, such as avoiding costly protecting groups and time-consuming purification procedures after each step. The explosive development of enantioselective metal-catalyzed domino including multicomponent reactions is a consequence of the considerable impact of the advent of asymmetric transition-metal catalysis. This review aims to update the last developments of enantioselective one-, two-and multicomponent domino reactions mediated by chiral metal catalysts, covering the literature since the beginning of 2006

show abstract

Cationic Palladium‐Catalyzed [5+2] Annulation: Synthesis of 1‐Benzoxepines from 2‐Aroylmethoxyarylboronic Acids

Abstract: (TfO À ) 2 was developed. This [5 + 2] annulation involves the intramolecular nucleophilic addition of a vinylpalladium species to ketones.

Cited by 46 publications

References 47 publications

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Renoprotective effect of Tanshinone IIA, an active component of Salvia miltiorrhiza, on rats with chronic kidney disease

Protodepalladation as a Strategic Elementary Step in Catalysis

Recent Developments in Enantioselective Metal‐Catalyzed Domino Reactions

Contact Info

Product

Resources

About