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17 Mar 02:01

Bridged [2.2.1] bicyclic phosphine oxide facilitates catalytic [gamma]-umpolung addition-Wittig olefination

Chem. Sci., 2018, 9,1867-1872
DOI: 10.1039/C7SC04381C, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Kui Zhang, Lingchao Cai, Zhongyue Yang, K. N. Houk, Ohyun Kwon
A bridged [2.2.1] bicyclic phosphine oxide has been created and applied successfully in halide-/base-free catalytic [gamma]-umpolung addition-Wittig olefinations.
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17 Oct 10:34

Coupling Reaction of Cu-Based Carbene and Nitroso Radical: A Tandem Reaction To Construct Isoxazolines

by Rongxiang Chen, Yanwei Zhao, Shangwen Fang, Wenhao Long, Hongmei Sun and Xiaobing Wan

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Organic Letters
DOI: 10.1021/acs.orglett.7b02885
17 Oct 10:16

Copper-Catalyzed C(sp2)–S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents

by Zhi-Bing Dong, Xing Liu and Carsten Bolm

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Organic Letters
DOI: 10.1021/acs.orglett.7b02911
11 Oct 15:22

Applications of [4+2] Anionic Annulation and Carbonyl-Ene Reaction in the Synthesis of Anthraquinones, Tetrahydroanthraquinones, and Pyranonaphthoquinones

by Shyam Basak and Dipakranjan Mal

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01987
17 Sep 10:10

From Simple to Complex: Rhodium(III)-Catalyzed C–C Bond Cleavage and C–H Bond Functionalization for the Synthesis of 3a,8b-Dihydro-1H-cyclopenta[b]benzofuran-1-ones

by Guiyu Guo, Saihong Wan, Xiaodong Si, Qijian Jiang, Yuanyuan Jia, Luo Yang and Wang Zhou

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Organic Letters
DOI: 10.1021/acs.orglett.7b02052
05 Mar 06:51

A Four-Component Cascade C–H Functionalization/Cyclization/Nucleophilic Substitution Reaction To Construct α-Functionalized Tetrahydroquinolines by the Strategy of in Situ Directing Group Formation

by Peng Bai, Ya-Qiong Li and Zhi-Zhen Huang

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Organic Letters
DOI: 10.1021/acs.orglett.7b00226
12 Nov 03:18

Catalytic [2+2+1] Synthesis of Fused Thiophenes Using Thiocarbonyls as Sulfur Donors

by Kazuma Matsui, Masatoshi Shibuya, Yoshihiko Yamamoto

Abstract

The use of N-(p-chlorophenyl)methylbenzoxazole-2-thione as a sulfur-atom donor enables the catalytic [2+2+1] cycloaddition of diynes in wet DMF at 80 °C when open to air, thus affording diverse fused thiophenes with good yields and wide functional-group compatibility. A plausible mechanism, involving a cationic ruthenacycle intermediate, was also proposed on the basis of several control experiments.

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The use of N-(p-chlorophenyl)methylbenzoxazole-2-thione as a sulfur-atom donor enables the catalytic [2+2+1] cycloaddition of diynes in DMF at 80 °C when open to air, thus affording diverse fused thiophenes with good yields and wide functional-group compatibility. A plausible mechanism, involving a cationic ruthenacycle intermediate, was also proposed on the basis of several control experiments.

12 Nov 03:14

Copper-Catalyzed Direct Coupling of Unprotected Propargylic Alcohols with P(O)H Compounds: Access to Allenylphosphoryl Compounds under Ligand- and Base-Free Conditions

by Gaobo Hu, Changkai Shan, Weizhu Chen, Pengxiang Xu, Yuxing Gao and Yufen Zhao

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Organic Letters
DOI: 10.1021/acs.orglett.6b03028
21 Oct 14:07

Integration of aerobic oxidation and intramolecular asymmetric aza-Friedel-Crafts reactions with a chiral bifunctional heterogeneous catalyst

Chem. Sci., 2016, Advance Article
DOI: 10.1039/C6SC03849B, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Hong-Gang Cheng, Javier Miguelez, Hiroyuki Miyamura, Woo-Jin Yoo, Shu Kobayashi
A chiral heterogeneous material was prepared and evaluated as a bifunctional catalyst for the sequential aerobic oxidation-asymmetric intramolecular aza-Friedel-Crafts reaction.
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12 Sep 02:48

Enantioselective Nucleophilic β-Carbon-Atom Amination of Enals: Carbene-Catalyzed Formal [3+2] Reactions

by Xingxing Wu, Bin Liu, Yuexia Zhang, Martin Jeret, Honglin Wang, Pengcheng Zheng, Song Yang, Bao-An Song, Yonggui Robin Chi

Abstract

An enantioselective β-carbon amination for enals is disclosed. The nitrogen atom from a protected hydrazine with suitable electronic properties readily behaves as a nucleophile. Addition of the nitrogen nucleophile to a catalytically generated N-heterocyclic-carbene-bound α,β-unsaturated acyl azolium intermediate constructs a new carbon–nitrogen bond asymmetrically. The pyrazolidinone products from our catalytic reactions are common scaffolds in bioactive molecules, and can be easily transformed into useful compounds such as β3-amino-acid derivatives.

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Focus on the β-C: The aza-Michael addition of protected hydrazine to a catalytically generated unsaturated acyl azolium intermediate provides a highly efficient approach for enantioselective β-carbon-atom amination of enals. The heterocyclic products, prepared by using this method, are common scaffolds found in bioactive molecules, and can be readily transformed into β3-amino-acid derivatives. NHC=N-heterocyclic carbene.

20 Jun 16:33

Metal-Free Oxidative Annulation of 2-Naphthols with Terminal Alkynes Affording 2-Arylnaphtho[2,1-b]furans

by Long Liu, Xuyu Ji, Jianyu Dong, Yongbo Zhou and Shuang-Feng Yin

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Organic Letters
DOI: 10.1021/acs.orglett.6b01352
28 Dec 16:26

Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C–H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole

by Wangqing Kong, Qian Wang and Jieping Zhu

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Journal of the American Chemical Society
DOI: 10.1021/jacs.5b11625
09 Oct 15:45

Pd(0)-Catalyzed Carbene Insertion into Si–Si and Sn–Sn Bonds

by Zhenxing Liu, Haocheng Tan, Tianren Fu, Ying Xia, Di Qiu, Yan Zhang and Jianbo Wang
gengxiao

attention

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Journal of the American Chemical Society
DOI: 10.1021/jacs.5b09135