Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation

Yu, Zhunzhun; Qiu, Haile; Liu, Lu; Zhang, Junliang

doi:10.1039/c5cc08880a

Cited by 76 publications

(19 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Yu and coworkers synthesized indanols 145 having two adjacent stereo centers by gold‐catalyzed cross coupling of an aryl ketone 144 and a diazoester 143 (Scheme ) . The reaction involves a sequential Friedel‐Craft alkylation and an annulation strategy in a tandem manner.…”

Section: Gold‐catalyzed Csp2−h Bond Activation Processesmentioning

confidence: 99%

“…Yu and coworkers synthesized indanols 145 having two adjacent stereo centers by gold-catalyzed cross coupling of an aryl ketone 144 and a diazoester 143 (Scheme 34). [34] The reaction involves a sequential Friedel-Craft alkylation and an annulation strategy in a tandem manner. Under the optimized conditions (2,4-t BuC 6 H 4 O) 3 PAuNTf 2 catalyst in DCM at room temperature) different ketones were reacted with various phenyl α-diazoesters giving the corresponding indanols in moderate to good yields (44-85%)…”

Section: Gold-catalyzed Coupling Reactions Through Csp 2 à H Bond Actmentioning

confidence: 99%

See 1 more Smart Citation

Advances and Prospects in Gold‐Catalyzed C−H Activation

et al. 2020

View full text Add to dashboard Cite

The omnipresent character of C−H bonds in organic molecules gives a wide variety of opportunities for the synthesis of a number of functionalized molecules by the activation of the C−H bonds. One of those methods is gold‐catalyzed C−H activation. Recent developments in the area of gold‐catalyzed C−H activation involves annulation reactions leading to the formation of heterocyclic compounds, Au‐catalyzed cross coupling reactions, and C−H functionalization reactions with high atom efficiency. In this short review we summarize the developments and studies carried out in gold‐catalyzed C−H activation over the past decade.

show abstract

Section: Gold‐catalyzed Csp2−h Bond Activation Processesmentioning

confidence: 99%

Section: Gold-catalyzed Coupling Reactions Through Csp 2 à H Bond Actmentioning

confidence: 99%

Advances and Prospects in Gold‐Catalyzed C−H Activation

et al. 2020

View full text Add to dashboard Cite

show abstract

“…[41] Both five-and six-memberedr ings could be synthesized in good yields and diastereoselectivities. [41] Both five-and six-memberedr ings could be synthesized in good yields and diastereoselectivities.…”

Section: Alkylation With Diazoacetatesmentioning

confidence: 99%

Recent Advances in Gold‐Catalyzed Intermolecular Aryl C−H Functionalization

Kramer

2016

Chemistry A European J

View full text Add to dashboard Cite

The direct and selective functionalization of C-H bonds offers a powerful opportunity for greener and shorter routes to valuable chemicals. While still in its infancy, research exploiting the unique features of gold catalysis for the functionalization of aryl C-H bonds has demonstrated great potential for facile regioselective decoration of (hetero)arenes. Particularly within the last five years, a more general strategy for utilizing oxidative gold catalysis has emanated including an improved understanding of the underlying mechanistic pathways. To encourage and facilitate further research in intermolecular C-H functionalization of arenes with homogeneous gold catalysis, this Minireview critically presents the transformations and mechanistic data available within this field.

show abstract

“…Very recently,acascade reaction leading to the formation of two contiguous stereocenters, one of which is all-carbon substituted, was reportedb yZ hang and co-workers (Scheme 15). [41] Both five-and six-memberedr ings could be synthesized in good yields and diastereoselectivities. The reaction is proposed to proceed by initial nucleophilic addition of the arene to the electrophilic gold-carbenoids pecies, similart o the mechanism in Scheme 14.…”

Section: Alkylation With Diazoacetatesmentioning

confidence: 99%

ChemInform Abstract: Recent Advances in Gold‐Catalyzed Intermolecular Aryl C—H Functionalization

Kramer

2016

ChemInform

View full text Add to dashboard Cite

The direct ands electivef unctionalization of CÀH bonds offers ap owerful opportunity for greener and shorter routes to valuable chemicals. While still in its infancy,r esearch exploiting the unique features of gold catalysis for the functionalization of aryl CÀHb onds has demonstrated great potentialf or facile regioselective decoration of (hetero)arenes. Particularly within the last five years, am ore gener-al strategy for utilizingo xidative gold catalysis has emanated including an improved understandingo ft he underlying mechanistic pathways. To encourage andfacilitate further research in intermolecularC ÀHf unctionalization of arenes with homogeneous gold catalysis, this Minireview critically presents the transformationsa nd mechanistic data available within this field. Scheme1.Different pathways in gold-catalyzed aryl CÀHf unctionalization. (Nu = nucleophile, R.E. = reductive elimination, E = electrophile, and EAS = electrophilic aromatic substitution).[a] Dr.SørenK ramer obtained his PhD from Aarhus University in 2012 working with homogeneous gold catalysisu nder the supervisiono f Prof. Troels Skrydstrup. His graduate studies included stays at École Polytechnique and University of North Carolina at Chapel Hill. During 2013-2015, Søren conducted post-doctoral research in the field of asymmetric organocatalysis with Prof. Gregory C. Fu at California Institute of Technology.N ow,S øreni s apostdoctoral researcher at Aarhus University with Prof. T. Skrydstrup working with mechanistic elucidation of transition-metal-catalyzed reactions. Scheme2.Oxidative homocoupling of arenesbyT se et al. Scheme3.Oxidative cross-coupling of arenes by Russelle tal. (CSA = camphorsulfonic acid). Scheme4.Mechanistic investigation and proposed reaction mechanism for the aryl-aryl cross-coupling by Russell et al. (TOLS = turnover-limiting step).

show abstract

Gold-catalyzed construction of two adjacent quaternary stereocenters via sequential C–H functionalization and aldol annulation

Cited by 76 publications

References 58 publications

Advances and Prospects in Gold‐Catalyzed C−H Activation

Advances and Prospects in Gold‐Catalyzed C−H Activation

Recent Advances in Gold‐Catalyzed Intermolecular Aryl C−H Functionalization

ChemInform Abstract: Recent Advances in Gold‐Catalyzed Intermolecular Aryl C—H Functionalization

Contact Info

Product

Resources

About