- Palladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation
-
Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles has been accomplished using a readily available arene at moderate temperature. The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications are the important practical features.
- Basak, Shubhajit,Paul, Tripti,Punniyamurthy, Tharmalingam
-
supporting information
p. 554 - 558
(2022/01/20)
-
- A Nickel-Catalyzed Carbonyl-Heck Reaction
-
The use of transition-metal catalysis to enable the coupling of readily available organic molecules has greatly enhanced the ability of chemists to access complex chemical structures. In this work, an intermolecular coupling reaction that unites organotriflates and aldehydes is presented. A unique catalyst system is identified to enable this reaction, featuring a Ni0 precatalyst, a tridentate Triphos ligand, and a bulky amine base. This transformation provides access to a variety of ketone-containing products without the selectivity- and reactivity-related challenges associated with more traditional Friedel–Crafts reactions. A Heck-type mechanism is postulated, wherein the π bond of the aldehyde takes the role of the olefin in the insertion/elimination steps.
- Vandavasi, Jaya Kishore,Hua, XiYe,Halima, Hamdi Ben,Newman, Stephen G.
-
supporting information
p. 15441 - 15445
(2017/11/10)
-
- Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives
-
A method for the oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary stereocenters in good to excellent yields via sequential intramolecular oxidative arylacetoxylation, hydrolysis and oxidation steps.
- Karnakanti, Shuklachary,Zang, Zhong-Lin,Zhao, Sheng,Shao, Pan-Lin,Hu, Ping,He, Yun
-
supporting information
p. 11205 - 11208
(2017/10/17)
-
- Carbonylative suzuki couplings of aryl bromides with boronic acid derivatives under base-free conditions
-
The carbonylative Suzuki-Miyaura reaction between aryl bromides and arylboronic acid equivalents is herein reported, using base-free conditions and a limited excess of carbon monoxide generated ex situ from stable CO-precursors. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and its 13C-labeled derivative in good yields from the appropriate CO-precursor.
- Bjerglund, Klaus M.,Skrydstrup, Troels,Molander, Gary A.
-
supporting information
p. 1888 - 1891
(2014/05/06)
-
- Nucleophilic addition of grignard reagents to 3-acylindoles: Stereoselective synthesis of highly substituted indoline scaffolds
-
3-Acylindoles undergo nucleophilic-type reactions with Grignard reagents to efficiently afford either cis- or trans-substituted indolines, depending on the different quenching procedures. The enolate intermediate could be trapped by aryl acyl chlorides to provide indolines bearing a quaternary carbon center with high stereoselectivity. In contrast, the use of benzyl bromide as an electrophile results in the fragmentation of the indole ring. The indoline products could be easily transformed into indoles through oxidation with DDQ in a one-pot manner.
- Wang, Lu,Shao, Yushang,Liu, Yuanhong
-
supporting information; experimental part
p. 3978 - 3981
(2012/10/08)
-