Organic Letters
DOI: 10.1021/acs.orglett.5b00830
Darren Poole
Shared posts
27 Apr 09:49
Decarboxylative Alkynyl Termination of Palladium-Catalyzed Catellani Reaction: A Facile Synthesis of α-Alkynyl Anilines via Ortho C–H Amination and Alkynylation
by Fenggang Sun and Zhenhua Gu
27 Apr 09:22
A General Method for Imine Formation Using B(OCH2CF3)3
by Jonathan T. Reeves, Michael D. Visco, Maurice A. Marsini, Nelu Grinberg, Carl A. Busacca, Anita E. Mattson and Chris H. Senanayake
Organic Letters
DOI: 10.1021/acs.orglett.5b00949
wangruijia, Windy and -1 others like this
27 Apr 06:58
Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains
by Alexander M. Taylor, Rishi G. Vaswani, Victor S. Gehling, Michael C. Hewitt, Yves Leblanc, James E. Audia, Steve Bellon, Richard T. Cummings, Alexandre Côté, Jean-Christophe Harmange, Hari Jayaram, Shivangi Joshi, Jose M. Lora, Jennifer A. Mertz, Adrianne Neiss, Eneida Pardo, Christopher G. Nasveschuk, Florence Poy, Peter Sandy, Jeremy W. Setser, Robert J. Sims, Yong Tang and Brian K. Albrecht
ACS Medicinal Chemistry Letters
DOI: 10.1021/ml500411h
27 Apr 06:58
Volume of Distribution in Drug Design
by Dennis A. Smith, Kevin Beaumont, Tristan S. Maurer and Li Di
Journal of Medicinal Chemistry
DOI: 10.1021/acs.jmedchem.5b00201
27 Apr 06:58
Palladium(0)/PAr3-Catalyzed Intermolecular Amination of C(sp3)H Bonds: Synthesis of β-Amino Acids
by Jian He, Toshihiko Shigenari, Jin-Quan Yu
Abstract
An intermolecular C(sp3)![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
H amination using a Pd0/PAr3 catalyst was developed. The reaction begins with oxidative addition of R2NOBz to a Pd0/PAr3 catalyst and subsequent cleavage of a C(sp3)H bond by the generated PdNR2 intermediate. The catalytic cycle proceeds without the need for external oxidants in a similar manner to the extensively studied palladium(0)-catalyzed CH arylation reactions. The electron-deficient triarylphosphine ligand is crucial for this C(sp3)H amination reaction to occur.
Zero in: The title reaction begins with oxidative addition of R2NOBz to a Pd0/PAr3 catalyst and subsequent cleavage of a C(sp3)H bond by the generated PdNR2 intermediate. The catalytic cycle proceeds without the need for external oxidants. The electron-deficient triarylphosphine ligand is crucial for this C(sp3)H amination reaction to occur. Bz=benzoyl.
27 Apr 06:56
Catalytic Chemical Amide Synthesis at Room Temperature: One More Step Toward Peptide Synthesis
by Tharwat Mohy El Dine, William Erb, Yohann Berhault, Jacques Rouden and Jérôme Blanchet
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00378
古月, Alex Jeanneret and one other like this
27 Apr 06:55
Synthesis of Five-, Six-, and Seven-Membered 1,3- and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols
by Manash J. Deka, Kiran Indukuri, Sabera Sultana, Madhurjya Borah and Anil K. Saikia
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00049
lkxingkong likes this
27 Apr 06:55
Late-Stage Functionalization of 1,2-Dihydro-1,2-azaborines via Regioselective Iridium-Catalyzed C–H Borylation: The Development of a New N,N-Bidentate Ligand Scaffold
by Andrew W. Baggett, Monica Vasiliu, Bo Li, David A. Dixon and Shih-Yuan Liu
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b01916
27 Apr 06:55
Nickel-Catalyzed Cross-Coupling of Photoredox-Generated Radicals: Uncovering a General Manifold for Stereoconvergence in Nickel-Catalyzed Cross-Couplings
by Osvaldo Gutierrez, John C. Tellis, David N. Primer, Gary A. Molander and Marisa C. Kozlowski
Journal of the American Chemical Society
DOI: 10.1021/ja513079r
27 Apr 06:54
Palladium-Catalyzed One-Pot Sonogashira Coupling, exo-dig Cyclization and Hydride Transfer Reaction: Synthesis of Pyridine-Substituted Pyrroles
by Kommuri Shekarrao, Partha Pratim Kaishap, Sanjib Gogoi, Romesh C. Boruah
Abstract
An efficient palladium(II)-catalyzed method for the synthesis of alkylated pyridine-substituted pyrroles has been developed by a one-pot three component reaction of β-bromovinyl aldehydes, primary amines and 2-alkynylpyridines in good yields. The reactions can also provide an efficient route to 2-picolinoylpyrroles by slightly altering the reaction conditions.
cxl likes this
15 Apr 06:50
LP99: Discovery and Synthesis of the First Selective BRD7/9 Bromodomain Inhibitor
by Peter G. K. Clark, Lucas C. C. Vieira, Cynthia Tallant, Oleg Fedorov, Dean C. Singleton, Catherine M. Rogers, Octovia P. Monteiro, James M. Bennett, Roberta Baronio, Susanne Müller, Danette L. Daniels, Jacqui Méndez, Stefan Knapp, Paul E. Brennan, Darren J. Dixon
BRD7 and BRD9 are bromodomain proteins and part of some chromatin-remodeling complexes. A fragment lead was rapidly optimized through structure-based design and exploitation of a stereoselective nitro-Mannich/lactamization cascade process to give the first potent and selective BRD7/9 inhibitor, LP99. Treatment with LP99 led to displacement of BRD7 and BRD9 from chromatin and down-regulation of the pro-inflammatory cytokine IL-6.
[Communication]
Peter G. K. Clark, Lucas C. C. Vieira, Cynthia Tallant, Oleg Fedorov, Dean C. Singleton, Catherine M. Rogers, Octovia P. Monteiro, James M. Bennett, Roberta Baronio, Susanne Müller, Danette L. Daniels, Jacqui Méndez, Stefan Knapp, Paul E. Brennan, Darren J. Dixon
Angew. Chem. Int. Ed., April 13, 2015, DOI: 10.1002/anie.201501394. Read article.
15 Apr 06:50
Palladium-Catalyzed Asymmetric Reductive Heck Reaction of Aryl Halides
by Guizhou Yue, Kaining Lei, Hajime Hirao, Jianrong (Steve) Zhou
Hydrogen-bond donors promote halide dissociation from neutral arylpalladium halides to access an enantioselective cationic pathway. The use of trialkylammonium salts in a glycol solvent enables asymmetric reductive Heck reaction of aryl halides in high stereoselectivity.
[Communication]
Guizhou Yue, Kaining Lei, Hajime Hirao, Jianrong (Steve) Zhou
Angew. Chem. Int. Ed., April 13, 2015, DOI: 10.1002/anie.201501712. Read article.
15 Apr 06:49
Manganese-Catalyzed Late-Stage Aliphatic C–H Azidation
by Xiongyi Huang, Tova M. Bergsten and John T. Groves
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b01983
Han, jiachunman81 and 2 others like this
14 Apr 06:58
Organoborane Catalyzed Regioselective 1,4-Hydroboration of Pyridines
by Xiaoting Fan, Junhao Zheng, Zhen Hua Li and Huadong Wang
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b03147
Rebeca Arévalo, Amanda Bongers and 5 others like this
14 Apr 06:57
para-C–H Borylation of Benzene Derivatives by a Bulky Iridium Catalyst
by Yutaro Saito, Yasutomo Segawa and Kenichiro Itami
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b02052
Nyk, jiaxiaoxiao and 4 others like this
14 Apr 06:57
Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformation of Racemic Biaryls: Axial-to-Central Chirality Transfer
by Liu Yang, Huayu Zheng, Lei Luo, Jiang Nan, Jingjing Liu, Yaoyu Wang and Xinjun Luan
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b01285
lkxingkong, bianmingsioc and 7 others like this
09 Apr 13:26
Enantioselective A3 Reactions of Secondary Amines with a Cu(I)/Acid–Thiourea Catalyst Combination
by Chenfei Zhao and Daniel Seidel
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b02071
09 Apr 13:26
Dynamic Kinetic Asymmetric Amination of Alcohols: From A Mixture of Four Isomers to Diastereo- and Enantiopure α-Branched Amines
by Zi-Qiang Rong, Yao Zhang, Raymond Hong Bing Chua, Hui-Jie Pan and Yu Zhao
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b02212
lkxingkong, ccedil and 4 others like this
03 Apr 16:02
Ligand-Enabled Cross-Coupling of C(sp3)–H Bonds with Arylsilanes
by Jian He, Ryosuke Takise, Haiyan Fu and Jin-Quan Yu
Journal of the American Chemical Society
DOI: 10.1021/jacs.5b00890
03 Apr 15:44
Iridium-Catalyzed Chemoselective Reductive Nucleophilic Addition to N-Methoxyamides
by Minami Nakajima, Takaaki Sato and Noritaka Chida
Organic Letters
DOI: 10.1021/acs.orglett.5b00664
bianmingsioc, cxl likes this
03 Apr 15:43
β-Ketophosphonate Formation via Aerobic Oxyphosphorylation of Alkynes or Alkynyl Carboxylic Acids with H-Phosphonates
by Mingxin Zhou, Ming Chen, Yao Zhou, Kai Yang, Jihu Su, Jiangfeng Du and Qiuling Song
Organic Letters
DOI: 10.1021/acs.orglett.5b00574
jiaxiaoxiao, zhonghua lin and 5 others like this
03 Apr 15:42
Realized C–H Functionalization of Aryldiazo Compounds via Rhodium Relay Catalysis
by Lin Qiu, Daorui Huang, Guangyang Xu, Zhenya Dai and Jiangtao Sun
Organic Letters
DOI: 10.1021/acs.orglett.5b00674
Nyk, fang xinxin and 4 others like this
02 Apr 14:55
Trifluoromethyl Sulfoxides from Allylic Alcohols and Electrophilic SCF3 Donor by [2,3]-Sigmatropic Rearrangement
by Mayaka Maeno, Norio Shibata and Dominique Cahard
Organic Letters
DOI: 10.1021/acs.orglett.5b00750
wangruijia and -1 others like this
02 Apr 14:39
Silyloxide-Promoted Diastereoselective Addition of Aryl and Heterocyclic Trimethylsilanes to N-tert-Butanesulfinylimines
by Manas Das and Donal F. O’Shea
Organic Letters
DOI: 10.1021/acs.orglett.5b00697
02 Apr 14:39
Asymmetric Robinson-Type Annulation Reaction between β-Ketoamides and α,β-Unsaturated Ketones
by You-ming Huang, Chang-wu Zheng and Gang Zhao
The Journal of Organic Chemistry
DOI: 10.1021/jo502904n
lxw, jiachunman81 and -1 others like this
02 Apr 14:38
Palladium(II)-Catalyzed Directed Trifluoromethylthiolation of Unactivated C(sp3)–H Bonds
by Heng-Ying Xiong, Tatiana Besset, Dominique Cahard and Xavier Pannecoucke
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00505
fang xinxin, cyymumumao and one other like this
02 Apr 14:38
Iridium-Catalyzed Single-Step N-Substituted Lactam Synthesis from Lactones and Amines
by Kicheol Kim and Soon Hyeok Hong
Darren PooleI would like this, wouldn't I?
The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b00101
02 Apr 14:35
A Highly Efficient Gold-Catalyzed Photoredox α-C(sp3)-H Alkynylation of Tertiary Aliphatic Amines with Sunlight
by Jin Xie, Shuai Shi, Tuo Zhang, Nina Mehrkens, Matthias Rudolph, A. Stephen K. Hashmi
Golden sunshine: With 1-iodoalkynes as radical alkynylation reagents, unactivated tertiary aliphatic amines react in the presence of [Au2(μ-dppm)2]2+ (dppm=bis(diphenylphosphanyl)methane) in sunlight to afford propargylamines. A C-C coupling of an α-aminoalkyl radical and an alkynyl radical was proposed as the mechanism.
[Communication]
Jin Xie, Shuai Shi, Tuo Zhang, Nina Mehrkens, Matthias Rudolph, A. Stephen K. Hashmi
Angew. Chem. Int. Ed., March 30, 2015, DOI: 10.1002/anie.201412399. Read article.
02 Apr 14:35
Cyclic Hypervalent Iodine Reagents and Iron Catalysts: The Winning Team for Late-Stage C-H Azidation
by Maria Victoria Vita, Jerome Waser
1+1=3: By combining the exceptional reactivities of cyclic hypervalent iodine reagents and iron catalysts, Sharma and Hartwig achieved the azidation of C-H bonds with unprecedented efficiency and selectivity. The late-stage introduction of azides into complex bioactive molecules will greatly facilitate the synthesis of analogues and accelerate the discovery of new chemical entities.
[Highlight]
Maria Victoria Vita, Jerome Waser
Angew. Chem. Int. Ed., March 30, 2015, DOI: 10.1002/anie.201501666. Read article.
01 Apr 15:38
Palladium-Catalyzed C–H Functionalization of Acyldiazomethane and Tandem Cross-Coupling Reactions
by Fei Ye, Shuanglin Qu, Lei Zhou, Cheng Peng, Chengpeng Wang, Jiajia Cheng, Mohammad Lokman Hossain, Yizhou Liu, Yan Zhang, Zhi-Xiang Wang and Jianbo Wang
Journal of the American Chemical Society
DOI: 10.1021/ja513275c