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17 Aug 08:24

Experimental and Theoretical Quantification of the Lewis Acidity of Iodine(III) Species

by Axel Labattut, Pierre-Luc Tremblay, Odile Moutounet and Claude Y. Legault

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01616
12 Jul 10:06

Silver-Catalyzed Stereoselective Aminosulfonylation of Alkynes

Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes

Controllable assembly: The first intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN3 is reported. This three-component coupling, which shows excellent functional group tolerance, proceeds through sequential hydroazidation of the terminal alkyne and addition of a sulfonyl radical to the resultant vinyl azide. This enables the stereoselective synthesis of a wide range of β-sulfonyl N-unprotected enamines.

[Communication]
Yongquan Ning, Qinghe Ji, Peiqiu Liao, Edward A. Anderson, Xihe Bi
Angew. Chem. Int. Ed., July 07, 2017, https://doi.org/10.1002/anie.201705122 Read article

28 Jun 11:50

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki–Miyaura Cross-Coupling Reactions of Amides

by Peng Lei, Guangrong Meng, Yun Ling, Jie An and Michal Szostak

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00749
28 Jun 11:49

Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives

by Kensuke Kiyokawa, Tomoki Watanabe, Laura Fra, Takumi Kojima and Satoshi Minakata

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b01202
28 Jun 11:49

Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes

by Liang-Wei Qian, Mengli Sun, Jianyu Dong, Qing Xu, Yongbo Zhou and Shuang-Feng Yin

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00899
27 Jun 07:31

Photoinduced Oxidative Formylation of N,N-Dimethylanilines with Molecular Oxygen without External Photocatalyst

by Shuai Yang, Pinhua Li, Zhihui Wang and Lei Wang

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Organic Letters
DOI: 10.1021/acs.orglett.7b01230
27 Jun 07:31

Suzuki–Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N–C Cleavage

by Guangrong Meng, Roman Szostak and Michal Szostak

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Organic Letters
DOI: 10.1021/acs.orglett.7b01575
16 Jun 12:09

Catalytic Asymmetric Conjugate Addition of Indolizines to α,β-Unsaturated Ketones

Catalytic Asymmetric Conjugate Addition of Indolizines to α,β‐Unsaturated Ketones

Alkylated indolizines: Using (S)-TRIP as monofunctional catalyst, several alkylated indolizines were synthesized in good yields and with enantiomeric ratios of up to 98:2.

[Communication]
José Tiago Menezes Correia, Benjamin List, Fernando Coelho
Angew. Chem. Int. Ed., June 01, 2017, https://doi.org/10.1002/anie.201700513 Read article

03 May 08:13

C–H Functionalization of Azines

by Kei Murakami, Shuya Yamada, Takeshi Kaneda and Kenichiro Itami

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Chemical Reviews
DOI: 10.1021/acs.chemrev.7b00021
03 May 08:10

A Heterogeneous Gold(I)-Catalyzed [2 + 2 + 1] Annulation of Terminal Alkynes, Nitriles, and Oxygen Atoms Leading to 2,5-Disubstituted Oxazoles

by Weisen Yang, Rongli Zhang, Feiyan Yi and Mingzhong Cai

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00386
03 May 08:10

Multiple Approaches to the In Situ Generation of Anhydrous Tetraalkylammonium Fluoride Salts for SNAr Fluorination Reactions

by Megan A. Cismesia, Sarah J. Ryan, Douglas C. Bland and Melanie S. Sanford

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.7b00481
03 May 08:09

Amide-Directed C−H Sodiation by a Sodium Hydride/Iodide Composite

Amide‐Directed C−H Sodiation by a Sodium Hydride/Iodide Composite

New direction: An amide-directed ortho and lateral C−H sodiation is enabled by sodium hydride (NaH) in the presence of either sodium iodide (NaI) or lithium iodide (LiI). The transient organosodium intermediates could be transformed into functionalized aromatic compounds.

[Communication]
Yinhua Huang, Guo Hao Chan, Shunsuke Chiba
Angew. Chem. Int. Ed., April 27, 2017, https://doi.org/10.1002/anie.201702512 Read article

03 May 08:08

Catalytic Desymmetrization by C−H Functionalization as a Solution to the Chiral Methyl Problem

Catalytic Desymmetrization by C−H Functionalization as a Solution to the Chiral Methyl Problem

Breaking the mirror (plane): A palladium-catalyzed desymmetrization strategy via β C−H activation provides an alternate approach for solving the age-old challenge of introducing an α-methyl stereocenter to a molecule.

[Highlight]
David A. Nagib
Angew. Chem. Int. Ed., April 28, 2017, https://doi.org/10.1002/anie.201703311 Read article

03 May 08:08

Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides

Chem. Sci., 2017, 8,4437-4442
DOI: 10.1039/C7SC00675F, Edge Article
Open Access Open Access
Tim Markovic, Benjamin N. Rocke, David C. Blakemore, Vincent Mascitti, Michael C. Willis
Pyridine sulfinates are stable and straightforward to prepare nucleophilic coupling partners for palladium catalyzed cross-coupling reactions with aryl and heteroaryl halides. The scope with respect to the halides coupling partner is considerable, and allows the preparation of a broad range of linked pyridines.
The content of this RSS Feed (c) The Royal Society of Chemistry
23 Jan 14:43

Difluoromethyl Bioisostere: Examining the “Lipophilic Hydrogen Bond Donor” Concept

by Yossi Zafrani, Dina Yeffet, Gali Sod-Moriah, Anat Berliner, Dafna Amir, Daniele Marciano, Eytan Gershonov and Sigal Saphier

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Journal of Medicinal Chemistry
DOI: 10.1021/acs.jmedchem.6b01691
17 Jan 08:21

Manganese-Catalyzed Multicomponent Synthesis of Pyrimidines from Alcohols and Amidines

Manganese‐Catalyzed Multicomponent Synthesis of Pyrimidines from Alcohols and Amidines

Something borrowed: A manganese complex stabilized by a PN5P-pincer ligand catalyzes the multicomponent synthesis of pyrimidines from amidines and up to three (different) alcohols. The consecutive 4-component reaction combines the concept of borrowing hydrogen or hydrogen autotransfer with dehydrogenation condensation to permit selective C−N and C−C bond formation.

[Communication]
Nicklas Deibl, Rhett Kempe
Angew. Chem. Int. Ed., January 12, 2017, DOI: 10.1002/anie.201611318. Read article

08 Nov 15:53

Combinations of Aminocatalysts and Metal Catalysts: A Powerful Cooperative Approach in Selective Organic Synthesis

by Samson Afewerki and Armando Córdova

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Chemical Reviews
DOI: 10.1021/acs.chemrev.6b00226
01 May 16:11

Chemoselective Ketone Synthesis by the Addition of Organometallics to N-Acylazetidines

by Chengwei Liu, Marcel Achtenhagen and Michal Szostak

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Organic Letters
DOI: 10.1021/acs.orglett.6b00842
03 Apr 11:10

The Development and Application of Two-Chamber Reactors and Carbon Monoxide Precursors for Safe Carbonylation Reactions

by Stig D. Friis, Anders T. Lindhardt and Troels Skrydstrup

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.5b00471
03 Apr 11:08

Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines

by Koji Kubota, Yuta Watanabe, Keiichi Hayama and Hajime Ito

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Journal of the American Chemical Society
DOI: 10.1021/jacs.6b01375
03 Apr 11:07

Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions

by Junhua Chen, Vignesh Palani and Thomas R. Hoye

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Journal of the American Chemical Society
DOI: 10.1021/jacs.6b01025
03 Apr 11:05

Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes

by Tejas K. Shah, Jose M. Medina and Neil K. Garg

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Journal of the American Chemical Society
DOI: 10.1021/jacs.6b01986
01 Apr 07:33

Regioselective Synthesis of 3-Hydroxy-4,5-alkyl-Substituted Pyridines Using 1,3-Enynes as Alkynes Surrogates

by Manuel Barday, Kelvin Y. T. Ho, Christopher T. Halsall and Christophe Aïssa

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Organic Letters
DOI: 10.1021/acs.orglett.6b00451
12 Mar 10:21

Iron-Catalyzed Regioselective Alkoxycarbonylation of Imidazoheterocycles with Carbazates

by Yongyuan Gao, Weiye Lu, Ping Liu and Peipei Sun

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00046
12 Mar 10:20

Mechanism of Rhodium-Catalyzed Formyl Activation: A Computational Study

by Xiaoling Luo, Ruopeng Bai, Song Liu, Chunhui Shan, Changguo Chen and Yu Lan

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b02828
12 Mar 10:19

HSiCl3-Mediated Reduction of Nitro-Derivatives to Amines: Is Tertiary Amine-Stabilized SiCl2 the Actual Reducing Species?

by Manuel Orlandi, Maurizio Benaglia, Filippo Tosi, Rita Annunziata and Franco Cozzi

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.6b00191
12 Mar 10:19

Insertion of N-Tosylacetimidates/Acetimidamides onto Arynes via [2 + 2] Cycloaddition

by Ramagonolla Kranthikumar, Rambabu Chegondi and Srivari Chandrasekhar

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b02907
12 Mar 10:18

One-Pot Synthesis of Arylketones from Aromatic Acids via Palladium-Catalyzed Suzuki Coupling

by Hongxiang Wu, Baiping Xu, Yue Li, Fengying Hong, Dezhao Zhu, Junsheng Jian, Xiaoer Pu and Zhuo Zeng

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.5b02667
10 Mar 13:22

Enantiospecific Alkynylation of Alkylboronic Esters

Enantiospecific Alkynylation of Alkylboronic Esters

Enantiospecific alkynylation: Enantioenriched secondary and tertiary alkyl pinacolboronic esters undergo enantiospecific deborylative alkynylation through a Zweifel-type alkenylation followed by a 1,2-elimination reaction to give alkynes in high yield and essentially complete enantiospecificity.

[Communication]
Yahui Wang, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal
Angew. Chem. Int. Ed., March 02, 2016, DOI: 10.1002/anie.201600599. Read article

10 Mar 13:19

Photoinduced Copper-Catalyzed C−H Arylation at Room Temperature

Photoinduced Copper‐Catalyzed C−H Arylation at Room Temperature

Copper light: Room-temperature C−H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C−H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.

[Communication]
Fanzhi Yang, Julian Koeller, Lutz Ackermann
Angew. Chem. Int. Ed., March 09, 2016, DOI: 10.1002/anie.201512027. Read article