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13 Mar 10:52

Copper-Catalyzed Highly Stereoselective Trifluoromethylation and Difluoroalkylation of Secondary Propargyl Sulfonates

by Xingang Zhang, Xing Gao, Yu-Lan Xiao, Xiaolong Wan

Abstract

It is challenging to stereoselectively introduce a trifluoromethyl group (CF3) into organic molecules. To date, only limited strategies involving direct asymmetric trifluoromethylation have been reported. Herein, we describe a new strategy for direct asymmetric trifluoromethylation through the copper-catalyzed stereospecific trifluoromethylation of optically active secondary propargyl sulfonates. The reaction enables propargylic trifluoromethylation with high regioselectivity and stereoselectivity. The reaction could also be extended to stereospecific propargylic difluoroalkylation. Transformations of the resulting enantiomerically enriched fluoroalkylated alkynes led to a variety of chiral fluoroalkylated compounds, thus providing a useful protocol for applications in the synthesis of fluorinated complexes.

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Just the beginning: The title reaction enables propargylic trifluoromethylation and difluoroalkylation with high regioselectivity and stereoselectivity (see scheme) to provide versatile building blocks that undergo a wide variety of transformations. Inversion of configuration was observed for the copper-catalyzed process, thus demonstrating that SN2-type oxidative addition of copper to the secondary propargyl sulfonate may be involved in the reaction.

14 Nov 09:06

Biocatalytic site- and enantioselective oxidative dearomatization of phenols

by Summer A. Baker Dockrey

Biocatalytic site- and enantioselective oxidative dearomatization of phenols

Biocatalytic site- and enantioselective oxidative dearomatization of phenols, Published online: 13 November 2017; doi:10.1038/nchem.2879

Within natural product biosynthetic pathways, nature has evolved highly selective catalysts capable of complexity generating reactions. Leveraging these tools, a suite of catalysts with complementary site- and stereoselectivity have been applied to the oxidative dearomatization of phenolic compounds, enabling one-pot transformations of phenols into various natural products.
13 Nov 11:38

Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2

by Yong-Yuan Gui, Naifu Hu, Xiao-Wang Chen, Li−Li Liao, Tao Ju, Jian-Heng Ye, Zhen Zhang, Jing Li and Da-Gang Yu

TOC Graphic

Journal of the American Chemical Society
DOI: 10.1021/jacs.7b10149
17 Oct 12:31

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Brønsted Acid and Palladium Catalysis

by Réka J. Faggyas, Ewen D. D. Calder, Claire Wilson and Andrew Sutherland

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b02287
22 Jun 07:57

Sequential Catalysis of Phosphine Oxide for Stereoselective Synthesis of Stereopentads

by Shunsuke Kotani, Kosuke Kai, Masaharu Sugiura and Makoto Nakajima

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Organic Letters
DOI: 10.1021/acs.orglett.7b01719
23 Nov 10:43

Pd-mediated cross-coupling of C-17 lithiated androst-16-en-3-ol - access to functionalized arylated steroid derivatives

Org. Biomol. Chem., 2016, Advance Article
DOI: 10.1039/C6OB02496C, Communication
Vanessa Koch, Stefan Brase
Herein, we report on Pd-mediated cross-coupling of vinyllithium steroids and aryl bromides to introduce various substituted aryls at C-17 of steroidal frameworks based on the structure of epi-androsterone.
To cite this article before page numbers are assigned, use the DOI form of citation above.
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15 Nov 07:26

Ce3+-Doped garnet phosphors: composition modification, luminescence properties and applications

Chem. Soc. Rev., 2017, 46,275-299
DOI: 10.1039/C6CS00551A, Review Article
Zhiguo Xia, Andries Meijerink
Crystal chemistry, luminescence and applications of Ce3+-doped garnets are reviewed and the tuning of optical properties is explained via combined insights from experiments and theory.
The content of this RSS Feed (c) The Royal Society of Chemistry
14 Nov 08:20

Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water

Chem. Sci., 2017, 8,1601-1606
DOI: 10.1039/C6SC04504A, Edge Article
Open Access Open Access
Dengfeng Chen, Qingyuan Feng, Yunqin Yang, Xu-Min Cai, Fei Wang, Shenlin Huang
Polyfunctional aromatic rings have been constructed by direct functionalization of C-H and O-H bonds to C-S and C-O bonds under mild and green conditions.
The content of this RSS Feed (c) The Royal Society of Chemistry
25 Oct 02:13

Doped Organic Transistors

by Björn Lüssem, Chang-Min Keum, Daniel Kasemann, Ben Naab, Zhenan Bao and Karl Leo

TOC Graphic

Chemical Reviews
DOI: 10.1021/acs.chemrev.6b00329
09 Sep 01:06

Hydrophobic substituents increase the potency of salacinol, a potent alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'

by Tanabe, Genzoh; Xie, Weijia; Balakishan, Gorre; et al.
Title: Hydrophobic substituents increase the potency of salacinol, a potent alpha-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'
Author(s): Tanabe, Genzoh; Xie, Weijia; Balakishan, Gorre; et al.
Source: BIOORGANIC & MEDICINAL CHEMISTRY, 24 (16): 3705-3715 AUG 15 2016
Document Type: Article
08 Jun 11:37

Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts

by Stephanie Kindt, Karina Wicht, Markus R. Heinrich

Abstract

The radical carbohydroxylation of styrenes with aryldiazonium salts has been achieved under mild thermal conditions. A broad range of aryldiazonium salts was tolerated, and the reaction principle based on a radical–polar crossover mechanism could be extended to carboetherification as well as to a two-step, metal-free variant of the Meerwein arylation leading to stilbenes.

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From radical to cation: The radical carbohydroxylation of styrenes with aryldiazonium salts has been achieved under mild thermal conditions. A broad range of aryldiazonium salts was tolerated and the reaction principle based on a radical–polar crossover mechanism could be extended to carboetherification as well as to a two-step, metal-free variant of the Meerwein arylation leading to stilbenes.

04 Jun 02:48

Peramivir Phosphonate Derivatives as Influenza Neuraminidase Inhibitors

by Peng-Cheng Wang, Jim-Min Fang, Keng-Chang Tsai, Shi-Yun Wang, Wen-I Huang, Yin-Chen Tseng, Yih-Shyun E. Cheng, Ting-Jen Rachel Cheng and Chi-Huey Wong

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Journal of Medicinal Chemistry
DOI: 10.1021/acs.jmedchem.6b00029
13 Apr 01:13

Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components

by Geraint H. M. Davies and Gary A. Molander

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00435
02 Aug 02:41

Bis(amino)cyclopropenylidene-Catalyzed 1,6-Conjugate Addition of Aromatic Aldehydes to para-Quinone Methides: Expedient Access to α,α′-Diarylated Ketones

by Bandaru T. Ramanjaneyulu, Sriram Mahesh and Ramasamy Vijaya Anand

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Organic Letters
DOI: 10.1021/acs.orglett.5b01724
31 Jul 05:50

Green Synthesis of Bifunctional Fluorescent Carbon Dots from Garlic for Cellular Imaging and Free Radical Scavenging

by Shaojing Zhao, Minhuan Lan, Xiaoyue Zhu, Hongtao Xue, Tsz-Wai Ng, Xiangmin Meng, Chun-Sing Lee, Pengfei Wang and Wenjun Zhang

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ACS Applied Materials & Interfaces
DOI: 10.1021/acsami.5b03228
04 Jun 01:15

Access to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction

Chem. Sci., 2015, 6,4807-4811
DOI: 10.1039/C5SC01460C, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Gustavo M. Borrajo-Calleja, Vincent Bizet, Thomas Burgi, Clement Mazet
A palladium catalyzed intermolecular asymmetric Heck reaction provides access to valuable 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter with high levels of regio- and enantiocontrol.
The content of this RSS Feed (c) The Royal Society of Chemistry
27 Mar 02:52

Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols

by Chuan Wang and Hisashi Yamamoto
大河弯弯的

帆哥?

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Journal of the American Chemical Society
DOI: 10.1021/jacs.5b01005
19 Mar 02:13

pleatedjeans:15 Unfortunate Cat Jump Fails

03 Mar 13:31

Pd-Catalyzed Directed ortho-C–H Alkenylation of Phenylalanine Derivatives

by Alfonso García-Rubia, Eduardo Laga, Carlos Cativiela, Esteban P. Urriolabeitia, Ramón Gómez-Arrayás and Juan C. Carretero

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The Journal of Organic Chemistry
DOI: 10.1021/jo502912m
03 Feb 02:12

Low-frequency and rare exome chip variants associate with fasting glucose and type 2 diabetes susceptibility

by Jennifer Wessel

Article

Both rare and common variants contribute to the aetiology of complex traits such as type 2 diabetes (T2D). Here, the authors examine the effect of coding variation on glycaemic traits and T2D, and identify low-frequency variation in GLP1R significantly associated with these traits.

Nature Communications doi: 10.1038/ncomms6897

Authors: Jennifer Wessel, Audrey Y Chu, Sara M Willems, Shuai Wang, Hanieh Yaghootkar, Jennifer A Brody, Marco Dauriz, Marie-France Hivert, Sridharan Raghavan, Leonard Lipovich, Bertha Hidalgo, Keolu Fox, Jennifer E Huffman, Ping An, Yingchang Lu, Laura J Rasmussen-Torvik, Niels Grarup, Margaret G Ehm, Li Li, Abigail S Baldridge, Alena Stančáková, Ravinder Abrol, Céline Besse, Anne Boland, Jette Bork-Jensen, Myriam Fornage, Daniel F Freitag, Melissa E Garcia, Xiuqing Guo, Kazuo Hara, Aaron Isaacs, Johanna Jakobsdottir, Leslie A Lange, Jill C Layton, Man Li, Jing Hua Zhao, Karina Meidtner, Alanna C Morrison, Mike A Nalls, Marjolein J Peters, Maria Sabater-Lleal, Claudia Schurmann, Angela Silveira, Albert V Smith, Lorraine Southam, Marcus H Stoiber, Rona J Strawbridge, Kent D Taylor, Tibor V Varga, Kristine H Allin, Najaf Amin, Jennifer L Aponte, Tin Aung, Caterina Barbieri, Nathan A Bihlmeyer, Michael Boehnke, Cristina Bombieri, Donald W Bowden, Sean M Burns, Yuning Chen, Yii-DerI Chen, Ching-Yu Cheng, Adolfo Correa, Jacek Czajkowski, Abbas Dehghan, Georg B Ehret, Gudny Eiriksdottir, Stefan A Escher, Aliki-Eleni Farmaki, Mattias Frånberg, Giovanni Gambaro, Franco Giulianini, William A Goddard, Anuj Goel, Omri Gottesman, Megan L Grove, Stefan Gustafsson, Yang Hai, Göran Hallmans, Jiyoung Heo, Per Hoffmann, Mohammad K Ikram, Richard A Jensen, Marit E Jørgensen, Torben Jørgensen, Maria Karaleftheri, Chiea C Khor, Andrea Kirkpatrick, Aldi T Kraja, Johanna Kuusisto, Ethan M Lange, I T Lee, Wen-Jane Lee, Aaron Leong, Jiemin Liao, Chunyu Liu, Yongmei Liu, Cecilia M Lindgren, Allan Linneberg, Giovanni Malerba, Vasiliki Mamakou, Eirini Marouli, Nisa M Maruthur, Angela Matchan, Roberta McKean-Cowdin, Olga McLeod, Ginger A Metcalf, Karen L Mohlke, Donna M Muzny, Ioanna Ntalla, Nicholette D Palmer, Dorota Pasko, Andreas Peter, Nigel W Rayner, Frida Renström, Ken Rice, Cinzia F Sala, Bengt Sennblad, Ioannis Serafetinidis, Jennifer A Smith, Nicole Soranzo, Elizabeth K Speliotes, Eli A Stahl, Kathleen Stirrups, Nikos Tentolouris, Anastasia Thanopoulou, Mina Torres, Michela Traglia, Emmanouil Tsafantakis, Sundas Javad, Lisa R Yanek, Eleni Zengini, Diane M Becker, Joshua C Bis, James B Brown, L Adrienne Cupples, Torben Hansen, Erik Ingelsson, Andrew J Karter, Carlos Lorenzo, Rasika A Mathias, Jill M Norris, Gina M Peloso, Wayne H.-H. Sheu, Daniela Toniolo, Dhananjay Vaidya, Rohit Varma, Lynne E Wagenknecht, Heiner Boeing, Erwin P Bottinger, George Dedoussis, Panos Deloukas, Ele Ferrannini, Oscar H Franco, Paul W Franks, Richard A Gibbs, Vilmundur Gudnason, Anders Hamsten, Tamara B Harris, Andrew T Hattersley, Caroline Hayward, Albert Hofman, Jan-Håkan Jansson, Claudia Langenberg, Lenore J Launer, Daniel Levy, Ben A Oostra, Christopher J O’Donnell, Stephen O’Rahilly, Sandosh Padmanabhan, James S Pankow, Ozren Polasek, Michael A Province, Stephen S Rich, Paul M Ridker, Igor Rudan, Matthias B Schulze, Blair H Smith, André G Uitterlinden, Mark Walker, Hugh Watkins, Tien Y Wong, Eleftheria Zeggini, Markku Laakso, Ingrid B Borecki, Daniel I Chasman, Oluf Pedersen, Bruce M Psaty, E Shyong Tai, Cornelia M van Duijn, Nicholas J Wareham, Dawn M Waterworth, Eric Boerwinkle, W H Linda Kao, Jose C Florez, Ruth J.F. Loos, James G Wilson, Timothy M Frayling, David S Siscovick, Josée Dupuis, Jerome I Rotter, James B Meigs, Robert A Scott, Mark O Goodarzi