Heterocycle Formation via Palladium-Catalyzed C-H Functionalization

Mei, Tian‐Sheng; Kou, Lei; Ma, Sandy; Engle, Keary M.; Yu, Jin‐Quan

doi:10.1055/s-0031-1289766

Cited by 153 publications

(12 citation statements)

References 144 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Later on, an improved procedure has been devised using at wofold excess of FeCl 3 which provides the corresponding alkenylated products in highery ields compared to those recorded using TFAasp romoter. [162] Under acidic conditions the protonated dimethylamino moiety behaves as ag ood leaving group for the nitroalkenylation of indoles (Scheme 83). [163] This procedure is promoted by TFAa nd has been mainly used for the synthesis of tryptamine derivatives which can be obtained by total reduction of the nitroethylene moiety.…”

Section: C-3 Alkenylationsmentioning

confidence: 99%

Regioselective Direct C‐Alkenylation of Indoles

Petrini

2017

Chemistry A European J

View full text Add to dashboard Cite

The direct introduction of alkenyl groups into the indole framework avoiding its preliminary functionalization can be carried out using different synthetic strategies. Transition-metal complexes facilitate the C-H activation of indoles or alkenes allowing an efficient Csp - Csp bond formation. The hydroindolation of alkynes catalyzed by the same metal complexes or various acidic promoters can also be pursued for the alkenylation process. Conjugate addition of electron-poor alkenes and direct condensation of carbonyl derivatives with indoles are also of interest for this purpose. The regiochemical control can be exploited using the intrinsic C-3 reactivity of the indole ring. The introduction of a suitable directing group at the nitrogen atom allows the preparation of C-2 alkenylated derivatives by transition metal catalyzed reactions. This review collects the fundamental contributions in this field reported in literature during the last fifteen years.

show abstract

Section: C-3 Alkenylationsmentioning

confidence: 99%

Regioselective Direct C‐Alkenylation of Indoles

Petrini

2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…In recent years, great advancements in transition metals catalyzed reactions provided synthetic organic chemists with many more tools to efficiently obtain heterocyclic molecules (Gulevich et al, 2013). In particular, the last decade saw enormous improvements in the available methodologies to activate and directly functionalize C–H bonds, and many of these methodologies indeed are specifically directed toward the synthesis of heterocycles (Thansandote and Lautens, 2009; Mei et al, 2012; Inamoto, 2013). However, these reactions typically require hazardous conditions and the use of common toxic organic solvents and suffer from procedural limitations such as the need of strictly anhydrous conditions.…”

Section: Introductionmentioning

confidence: 99%

Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds

et al. 2019

View full text Add to dashboard Cite

Herein we report the use of Rhodiasolv© Polarclean as a novel polar aprotic solvent for the synthesis of decorated heterocycles via dipolar cycloaddition (isooxazoles) or intramolecular C–H functionalization processes (benzo-fused chromenes). The use of Polarclean allowed to isolate the final products in good yields by simple solid filtration or liquid-liquid phase separation, avoiding the need for chromatographic purification. Moreover, since in the synthesis of benzo-fused chromenes, the metal catalyst is retained in Polarclean, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without any apparent loss in efficiency. This methodology is associated with a limited waste production. These results extend the applicability of Polarclean as a promising reaction medium for the replacement of toxic petrol-based solvent.

show abstract

“…In the last decades, research in this field has therefore been focused on the development of more efficient and selective strategies. In the current focus of heterocycle synthesis are C,H-activation with transition metal catalysts [5–8], oxidative cyclization using hypervalent iodine reagents [9–12], and homogeneously or heterogeneously catalyzed multicomponent reactions [13–14]. Moreover, radical cyclizations predominantly conducted using Bu 3 SnH in the presence of azobisisobutyronitrile (AIBN) play a crucial role [15–16].…”

Section: Introductionmentioning

confidence: 99%

Recent advances in the electrochemical construction of heterocycles

Francke

2014

Beilstein J. Org. Chem.

123

View full text Add to dashboard Cite

SummaryDue to the fact that the major portion of pharmaceuticals and agrochemicals contains heterocyclic units and since the overall number of commercially used heterocyclic compounds is steadily growing, heterocyclic chemistry remains in the focus of the synthetic community. Enormous efforts have been made in the last decades in order to render the production of such compounds more selective and efficient. However, most of the conventional methods for the construction of heterocyclic cores still involve the use of strong acids or bases, the operation at elevated temperatures and/or the use of expensive catalysts and reagents. In this regard, electrosynthesis can provide a milder and more environmentally benign alternative. In fact, numerous examples for the electrochemical construction of heterocycles have been reported in recent years. These cases demonstrate that ring formation can be achieved efficiently under ambient conditions without the use of additional reagents. In order to account for the recent developments in this field, a selection of representative reactions is presented and discussed in this review.

show abstract

Heterocycle Formation via Palladium-Catalyzed C-H Functionalization

Cited by 153 publications

References 144 publications

Regioselective Direct C‐Alkenylation of Indoles

Regioselective Direct C‐Alkenylation of Indoles

Polarclean as a Sustainable Reaction Medium for the Waste Minimized Synthesis of Heterocyclic Compounds

Recent advances in the electrochemical construction of heterocycles

Contact Info

Product

Resources

About