- Pd-Catalyzed Regio- and Stereoselective sp3 C?H Arylation of Primary Aliphatic Amines: Mechanistic Studies and Synthetic Applications
-
The Pd-catalyzed γ-position sp3?C?H arylation of primary amines bearing an aliphatic chain or cycloalkyl substituent and related mechanistic studies are disclosed. 3-Bromo-2-hydroxybenzaldehyde plays a key role in γ-position sp3?C?H arylation as a transient directing group (TDG) to assist the regio- and stereoselective C?H activation of a Pd catalyst, and the development of a tandem reaction to transform 1°-amines into γ-aryl-substituted ketones demonstrates synthetic utility. Density functional theory (DFT)-based calculations revealed the detailed reaction mechanism and the origins of the high selectivity (γ-position and cis-only). The X-ray crystal structure of the isolated endo-palladacycle intermediate supported the DFT results, and a kinetic isotope experiment confirmed the results of DFT calculations indicating that the C?H activation step via simultaneous palladation and deprotonation is rate-determining.
- Ha, Hyeonbin,Choi, Ho Jeong,Park, Hahyoun,Gwon, Yunyeong,Lee, Jiin,Kwak, Jaesung,Kim, Min,Jung, Byunghyuck
-
supporting information
p. 1136 - 1145
(2021/02/12)
-
- 7. 8 - dimethoxy - 2, 3, 4, 5 - tetrahydro - 1 H - benzo [c] azepine hydrochloride and its preparation method (by machine translation)
-
The invention discloses 7, 8 - dimethoxy - 2, 3, 4, 5 - tetrahydro - 1 H - benzo [c] azepine hydrochloride and its preparation method, in order to 3, 4 - dimethoxy c acid as initiator, in thionyl chloride catalytic, then ammonolysis to obtain 3, 4 - dimet
- -
-
-
- Investigation of dopamine analogues: Synthesis, mechanistic understanding, and structure-property relationship
-
Dopamine, perhaps the simplest molecule that covalently links catechol and amine, together with its derivatives, has shown impressive adhesive and coating properties with its polymers. However, the scope of the molecules is rather limited, and the polymer
- Hu, Huamin,Dyke, Jason Christopher,Bowman, Brett Allen,Ko, Ching-Chang,You, Wei
-
p. 9873 - 9882
(2016/10/07)
-
- Diverse alkaloid-like structures from a common building block
-
A wealth of unique enantiopure polycyclic alkaloid-like scaffolds can be prepared on a multigram scale in only a few steps from a common, commercially available intermediate. The attached nitromethyl group can then be used to construct highly diverse func
- Goff, Dane A.
-
p. 242 - 256
(2013/01/15)
-
- SYNTHESIS OF POLYCYCLIC ALKALOIDS
-
Disclosed embodiments concern polycyclic alkaloid compounds and methods for their use and synthesis. Particular embodiments concern polycyclic alkaloids having a fused, six-membered ring, while other embodiments concern polycyclic alkaloids having a fused
- -
-
Paragraph 0204
(2013/09/26)
-
- The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine
-
Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine. Georg Thieme Verlag Stuttgart.
- Vincze, Zoltan,Biro, A. Beatrix,Csekei, Marton,Timari, Geza,Kotschy, Andras
-
p. 1375 - 1385
(2007/10/03)
-
- Dopamine/serotonin receptor ligands VI. Dibenz[gj]-1-oxa-4-azacycloundecene and dibenz[d,g]-2-azacycloundecene: Synthesis of two new heterocyclic ring systems as potential ligands for dopamine receptor subtypes
-
2-(2-Hydroxyethyl)-N-[2-phenoxyethyl]benzamides and 2-(2-hydroxyethyl)-N-[2-phenylpropyl]benzamides have been prepared from 2-phenoxyethyl- or 2-phenylpropylamines and isochroman-1-one. Applying Bischler-Napieralski reaction, a tetracyclic isoquinolino[2,
- Wittig, Thomas W.,Enzensperger, Christorph,Lehmann, Jochen
-
p. 887 - 898
(2007/10/03)
-
- Phenylacetamide derivatives and pharmaceutical compositions thereof
-
The present invention provides novel phenylacetamide derivatives having the following formula STR1 wherein: X is a hydrogen, halogen, hydroxy, nitro, amino, R1, NR1 R2, NHR1 or OR1 wherein R1/su
- -
-
-
- Novel phenylacetamide derivatives and processes for the preparation thereof
-
The present invention provides novel phenylacetamide derivatives having the following formula wherein:, X is a hydrogen, halogen, hydroxy, nitro, amino, R1, NR1R2, NHR1 or OR1 wherein R1 and R2 are an optionally substituted C1 8 alky
- -
-
-
- Synthesis of Isoquinobenzazepines
-
A simple method for the synthesis of 12-alkoxyisoquinobenzazepines 6 in good yields starting from 3-(3-alkoxyphenyl)propylamines 1 and 1-isochromanone (2) is described.
- Meise, Werner,Schlueter, Gerd
-
p. 639 - 642
(2007/10/02)
-