- Bulky N-Heterocyclic-Carbene-Coordinated Palladium Catalysts for 1,2-Addition of Arylboron Compounds to Carbonyl Compounds
-
The synthesis of primary, secondary, and tertiary alcohols by the 1,2-addition of arylboronic acids or boronates to carbonyl compounds, including unactivated ketones, using novel bulky yet flexible N-heterocyclic carbene (NHC)-coordinated 2,6-di(pentan-3-yl)aniline (IPent)-based cyclometallated palladium complexes (CYPs) as catalysts is reported. The PhS-IPent-CYP-catalyzed reactions are efficient at low catalyst loadings (0.02–0.3 mol% Pd), and the exceptional catalytic activity for 1,2-addition is attributed to the steric bulk of the NHC ligand. These reactions can yield a wide range of functionalized benzylic alcohols that are difficult to synthesize by classical protocols using highly active organomagnesium or lithium reagents.
- Okuda, Yuta,Nagaoka, Masahiro,Yamamoto, Tetsuya
-
p. 6291 - 6300
(2020/11/30)
-
- Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments
-
gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.
- Croft, Rosemary A.,Dubois, Maryne A. J.,Boddy, Alexander J.,Denis, Camille,Lazaridou, Anna,Voisin-Chiret, Anne Sophie,Bureau, Ronan,Choi, Chulho,Mousseau, James J.,Bull, James A.
-
supporting information
p. 5385 - 5395
(2019/06/24)
-
- BMS-986163, a Negative Allosteric Modulator of GluN2B with Potential Utility in Major Depressive Disorder
-
There is a significant unmet medical need for more efficacious and rapidly acting antidepressants. Toward this end, negative allosteric modulators of the N-methyl-d-aspartate receptor subtype GluN2B have demonstrated encouraging therapeutic potential. We
- Marcin, Lawrence R.,Warrier, Jayakumar,Thangathirupathy, Srinivasan,Shi, Jianliang,Karageorge, George N.,Pearce, Bradley C.,Ng, Alicia,Park, Hyunsoo,Kempson, James,Li, Jianqing,Zhang, Huiping,Mathur, Arvind,Reddy, Aliphedi B.,Nagaraju,Tonukunuru, Gopikishan,Gupta, Grandhi V. R. K. M.,Kamble, Manjunatha,Mannoori, Raju,Cheruku, Srinivas,Jogi, Srinivas,Gulia, Jyoti,Bastia, Tanmaya,Sanmathi, Charulatha,Aher, Jayant,Kallem, Rajareddy,Srikumar, Bettadapura N.,Vijaya, Kumar Kuchibhotla,Naidu, Pattipati S.,Paschapur, Mahesh,Kalidindi, Narasimharaju,Vikramadithyan, Reeba,Ramarao, Manjunath,Denton, Rex,Molski, Thaddeus,Shields, Eric,Subramanian, Murali,Zhuo, Xiaoliang,Nophsker, Michelle,Simmermacher, Jean,Sinz, Michael,Albright, Charlie,Bristow, Linda J.,Islam, Imadul,Bronson, Joanne J.,Olson, Richard E.,King, Dalton,Thompson, Lorin A.,Macor, John E.
-
p. 472 - 477
(2018/05/23)
-
- Monoamine Oxidase (MAO-N) Whole Cell Biocatalyzed Aromatization of 1,2,5,6-Tetrahydropyridines into Pyridines
-
A sustainable MAO-N biocatalyzed process for the synthesis of pyridines from aliphatic tetrahydropyridines (THP) has been developed. Pyridine compounds were synthesized under mild reaction conditions and with high conversion, exploiting MAO-N whole cells as aromatizing biocatalysts. The kinetic profile of the whole cell biocatalytic transformation was finally investigated via in situ 19F NMR.
- Toscani, Anita,Risi, Caterina,Black, Gary W.,Brown, Nicola L.,Shaaban, Ali,Turner, Nicholas J.,Castagnolo, Daniele
-
p. 8781 - 8787
(2018/09/06)
-
- The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(III) complexes
-
A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L1-4H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1-7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502-560 nm.
- Davidson, Ross,Hsu, Yu-Ting,Batchelor, Thomas,Yufit, Dmitry,Beeby, Andrew
-
p. 11496 - 11507
(2016/07/26)
-
- (R)-3-((3S,4S)-3-FLUORO-4-(4-HYDROXYPHENYL)PIPERIDIN-1-YL)-1-(4-METHYLBENZYL)PYRROLIDIN-2-ONE AND ITS PRODRUGS FOR THE TREATMENT OF PSYCHIATRIC DISORDERS
-
The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the NR2B NMDA receptor and may be useful for the treatment of various disorders of
- -
-
Paragraph 0052-0053
(2015/07/15)
-
- Selective NR2B Antagonists
-
The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands of the NR2B receptor and may be useful for the treatment of various disorders of the c
- -
-
Paragraph 0142
(2015/07/15)
-
- Ni-catalysed, domino synthesis of tertiary alcohols from secondary alcohols
-
The use of in situ generated (NHC)-Ni catalytic species (NHC = N-heterocyclic carbene) allows for the synthesis, in short reaction times, of a variety of tertiary alcohols from secondary alcohols through a domino oxidation-addition protocol.
- Berini, Christophe,Navarro, Oscar
-
supporting information; experimental part
p. 1538 - 1540
(2012/02/16)
-
- COMPOUNDS AND COMPOSITIONS AS MODULATORS OF GPR119 ACTIVITY
-
The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of GPR119.
- -
-
Page/Page column 84-85
(2009/04/25)
-
- Design and synthesis of orally active inhibitors of TNF synthesis as anti-rheumatoid arthritis drugs
-
A novel series of TNF inhibitors was identified based on the screening of existing MMP inhibitor libraries. Further SAR optimization led to the discovery of a novel lead compound. Its synthesis, efficacy in experimental animal models, and pharmacokinetic
- Chen, Jian Jeffrey,Dewdney, Nolan,Lin, Xiaohong,Martin, Robert L.,Walker, Keith A. M.,Huang, Jane,Chu, Frances,Eugui, Elsie,Mirkovich, Anna,Kim, Yong,Sarma, Keshab,Arzeno, Humberto,Van Wart, Harold E.
-
p. 3951 - 3954
(2007/10/03)
-
- Synthesis and dopaminergic activity of some 3-(1,2,3,6-tetrahydro-1- pyridylalkyl)indoles. A novel conformational model to explain structure- activity relationships
-
The synthesis and dopaminergic properties of a novel type of dopamine agonist is described. The number and kind of essential structural elements differ significantly from that of the rigid apomorphine-type dopamine agonists. Using standard molecular modeling techniques, a conformational model is developed proposing a U-shaped conformation which might be energetically preferred through aromatic π-π-interactions between both of the electron rich aromatic structural elements of this class of compounds. Superimposition of conformations of the lead compound 28 with apomorphine yields a novel model explaining the atypical structure-activity relationships found in this class of indolealkylamines.
- Bottcher,Barnickel,Hausberg,Haase,Seyfried,Eiermann
-
p. 4020 - 4026
(2007/10/02)
-