Darren Poole

General vinylation strategy: α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, sulfoxides, and carbonyl derivatives has been achieved effectively by a one-pot C−H zincation and copper-catalyzed C(sp³)−C(sp²) cross-coupling reaction using vinylphenyliodonium salts under mild conditions.

[Communication]
Chuan Liu, Qiu Wang
Angew. Chem. Int. Ed., March 15, 2018, https://doi.org/10.1002/anie.201713278 Read article

Electro Co: Cobalt-catalyzed C−H/N−H functionalizations were accomplished without toxic metal oxidants by using electricity in H₂O at 23 °C. This sustainable cobalt electrocatalysis manifold proceeds with excellent levels of chemoselectivity and positional selectivity, and with ample scope.

[Communication]
Cong Tian, Leonardo Massignan, Tjark H. Meyer, Lutz Ackermann
Angew. Chem. Int. Ed., January 17, 2018, https://doi.org/10.1002/anie.201712647 Read article

Light instead of hydride: A photoredox process for reductive amination is reported, alongside substrate scope studies and in-depth mechanistic investigations. With this new method, reductive amination reactions can be conducted in a temporally and spatially controlled fashion, for example, on solid supports.

[Communication]
Xingwei Guo, Oliver S. Wenger
Angew. Chem. Int. Ed., January 18, 2018, https://doi.org/10.1002/anie.201711467 Read article

Light and water for a healthy reaction: Synergistic organophotoredox and nickel catalysis enabled the effective hydroxylation of aryl halides with water (see scheme), whereby deprotonation to form the OH group was facilitated by a base group on the ligand. This process, which does not require a strong inorganic base or a noble-metal catalyst, is suitable for the hydroxylation of multifunctional druglike aryl halides.

[Communication]
Liu Yang, Zhiyan Huang, Gang Li, Wei Zhang, Rui Cao, Chao Wang, Jianliang Xiao, Dong Xue
Angew. Chem. Int. Ed., January 24, 2018, https://doi.org/10.1002/anie.201710698 Read article

Simple and mild: A very bulky imidazole-based phosphine ligand enables the Barbier–Negishi coupling of secondary alkyl bromides with aryl and alkenyl triflates and nonaflates. This palladium-catalyzed reaction proceeeds at room temperature and provides the desired products with good chemoselectivity and limited isomerization.

[Communication]
Ke-Feng Zhang, Fadri Christoffel, Olivier Baudoin
Angew. Chem. Int. Ed., January 24, 2018, https://doi.org/10.1002/anie.201711990 Read article

Making light work: Commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen-atom-transfer catalyst under blue LED irradiation to provide polysubstituted aldehydes in one step. This strategy can be applied to structurally sophisticated substrates.

[Communication]
Fengjin Wu, Leifeng Wang, Jiean Chen, David A. Nicewicz, Yong Huang
Angew. Chem. Int. Ed., January 24, 2018, https://doi.org/10.1002/anie.201712384 Read article

A fluorosulfuryl imidazolium salt delivers the “F−SO₂+” fragment to Nu−H acceptor groups (phenols and amines) in various substrates. This new azolium triflate reagent reacts once with primary amines and anilines before the reaction stops. However, with triethylamine and two equivalents of the “F−SO₂+” donor present, it proceeds on to the bis(fluorosulfuryl) imide in good yield.

[Communication]
Taijie Guo, Genyi Meng, Xiongjie Zhan, Qian Yang, Tiancheng Ma, Long Xu, K. Barry Sharpless, Jiajia Dong
Angew. Chem. Int. Ed., January 25, 2018, https://doi.org/10.1002/anie.201712429 Read article

Taijie Guo, Genyi Meng, Xiongjie Zhan, Qian Yang, Tiancheng Ma, Long Xu, Prof. Dr. K. Barry Sharpless and Prof. Dr. Jiajia Dong

A fluorosulfuryl imidazolium salt delivers the “F−SO₂+” fragment to Nu−H acceptor groups (phenols and amines) in various substrates. This new azolium triflate reagent reacts once with primary amines and anilines before the reaction stops. However, with triethylamine and two equivalents of the “F−SO₂+” donor present, it proceeds on to the bis(fluorosulfuryl) imide in good yield.

Read more now

Feng Liu, Jia-Yin Wang, Peng Zhou, Prof. Dr. Guigen Li, Dr. Wen-Juan Hao, Prof. Shu-Jiang Tu and Prof. Dr. Bo Jiang

Just a DAB: A new metal-free [2+2] cycloaddition/S-centered radical induced 1,4-addition sequence of benzene-linked allene-ynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under convenient reaction conditions, thus providing practical access to functionalized cyclobuta[a]naphthalen-4-ols of chemical and biomedical importance. DABCO=1,4-diazabicyclo[2.2.2]octane.

Read more now

The best of both worlds: Diverse late transition metal catalysts can convert terminal or internal alkynes into transient allylmetal species that display electrophilic or nucleophilic properties. The use of alkynes as allylmetal precursors enables completely atom-efficient catalytic processes to be carried out, including enantioselective transformations.

[Minireview]
Alexander M. Haydl, Bernhard Breit, Tao Liang, Michael J. Krische
Angew. Chem. Int. Ed., August 10, 2017, https://doi.org/10.1002/anie.201704248 Read article

Nitro-Power! An exceptionally general electrophilic amination of zinc organyl compounds was developed, and yields alkylated aromatic aminoboranes from commercially available nitroarenes. The partially reduced nitro group is directly engaged as an electrophilic nitrogen intermediate. The aminoboranes were reacted with electrophiles, thereby incorporating two different substituents at the N atom of the former nitro group in a one-pot procedure.

[Communication]
Marian Rauser, Christoph Ascheberg, Meike Niggemann
Angew. Chem. Int. Ed., August 10, 2017, https://doi.org/10.1002/anie.201705356 Read article

An electrophilic shelf-stable monofluoromethylthiolating reagent, S-(fluoromethyl) benzenesulfonothioate (1), was developed. Reagent 1 couples with a variety of aryl boronic acids or unactivated alkenes to give the corresponding monofluoromethylthiolated arenes and alkanes in high yields.

[Communication]
Qunchao Zhao, Long Lu, Qilong Shen
Angew. Chem. Int. Ed., August 11, 2017, https://doi.org/10.1002/anie.201705633 Read article

Only with fluorine: A palladium-catalyzed cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates with (hetero)aryl boronic acids enables the stereoselective synthesis of more than twenty 1,1-diaryl-2,2,2-trifluoroethanes. The cross-coupling was shown to occur with predominant inversion of configuration.

[Communication]
Marta Brambilla, Matthew Tredwell
Angew. Chem. Int. Ed., August 15, 2017, https://doi.org/10.1002/anie.201706631 Read article