Shared posts

21 Jan 14:56

Greenwashed catalysis?

Nature Catalysis, Published online: 16 December 2022; doi:10.1038/s41929-022-00905-0

The 27th United Nations Climate Change Conference placed the risks of greenwashing under the spotlight. In this Editorial, we reflect on the implications of this phenomenon for science and peer review.
21 Jan 14:55

Boron-catalysed hydrogenolysis of unactivated C(aryl)–C(alkyl) bonds

by Yuliang Xu

Nature Catalysis, Published online: 23 December 2022; doi:10.1038/s41929-022-00888-y

Hydrogenolysis of unactivated C(aryl)–C(alkyl) bonds is a challenging task even in the presence of metal catalysts. Now, an approach using a boron catalyst is described that facilitates the hydrogenolysis of alkylarenes under mild conditions, and its utility is demonstrated by degrading polystyrene waste into benzene and phenylalkanes.
17 Jan 07:42

[ASAP] Dynamic Kinetic Resolution of β‑Substituted α‑Diketones via Asymmetric Transfer Hydrogenation

by Ting Chen, Wenjun Liu, Wei Gu, Shengtong Niu, Shouang Lan, Zhifei Zhao, Fan Gong, Jinggong Liu, Shuang Yang, Andrej Emanuel Cotman, Jinshuai Song, and Xinqiang Fang

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c11149
22 Dec 07:19

[ASAP] Kinetic Analysis of Consecutive/Parallel Transformation of Furfural to Biomass-Based Primary Amide by Using a “Concentration–Time” Integral

by Shengwen Yang and Jinzhu Chen
LongLarf

why

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ACS Catalysis
DOI: 10.1021/acscatal.2c03717
21 Dec 14:32

[ASAP] Ni(I)-Catalyzed Hydroxylation of Aryl Halides with Water under Thermal Catalysis

by Liu Yang, Yonggang Yan, Ni Cao, Jing Hao, Gang Li, Wei Zhang, Rui Cao, Chao Wang, Jianliang Xiao, and Dong Xue

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Organic Letters
DOI: 10.1021/acs.orglett.2c03840
21 Dec 14:29

[ASAP] Redesigning an (R)‑Selective Transaminase for the Efficient Synthesis of Pharmaceutical N‑Heterocyclic Amines

by Fulong Li, Yan Du, Youxiang Liang, Yuwen Wei, Yukun Zheng, and Huimin Yu

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ACS Catalysis
DOI: 10.1021/acscatal.2c05177
21 Dec 14:27

[ASAP] Turning Enantiomeric Relationships into Diastereomeric Ones: Self-Resolving α‑Ureidophosphonates and Their Organocatalytic Enantioselective Synthesis

by Vanda Dašková, Damián Padín, and Ben L. Feringa

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c10911
21 Dec 14:22

[ASAP] Reactivity and Enantioselectivity in NHC Organocatalysis Provide Evidence for the Complex Role of Modifications at the Secondary Sphere

by Zayed Alassad, Ashim Nandi, Sebastian Kozuch, and Anat Milo

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c08302
06 Dec 11:09

Efficient Synthesis of Novel Plasticizers by Direct Palladium‐Catalyzed Di‐ or Multi‐carbonylations

by Yuya Hu, Rui Sang, Robby Vroemans, Guillaume Mollaert, Rauf Razzaq, Helfried Neumann, Henrik Junge, Robert Franke, Ralf Jackstell, Bert Maes, Matthias Beller
Efficient Synthesis of Novel Plasticizers by Direct Palladium-Catalyzed Di- or Multi-carbonylations

The first di- and multi-carbonylations of olefins with di- or polyols provide a general and straightforward access to a variety of di- or multiesters with high efficiency and selectivity. Representative diesters show potential performance (T g) as novel plasticizers.


Abstract

Diesters are of fundamental importance in the chemical industry and are used for many applications, e.g. as plasticizers, surfactants, emulsifiers, and lubricants. Herein, we present a straightforward and efficient method for the selective synthesis of diesters via palladium-catalyzed direct carbonylation of di- or polyols with readily available alkenes. Key-to-success is the use of a specific palladium catalyst with the “built-in-base” ligand L16 providing esterification of all alcohols and a high n/iso ratio. The synthesized diesters were evaluated as potential plasticizers in PVC films by measuring the glass transition temperature (T g) via differential scanning calorimetry (DSC).

06 Dec 11:08

[ASAP] Directing-Group-Free Palladium-Catalyzed C–H Arylation of Aldoxime Using Oxime’s Umpolung Properties

by Kosaku Tanaka, III, Yoshimitsu Hashimoto, Nobuyoshi Morita, and Osamu Tamura

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Organic Letters
DOI: 10.1021/acs.orglett.2c03387
05 Dec 15:35

[ASAP] Novel Regioselective Approach to Cyclize Phage-Displayed Peptides in Combination with Epitope-Directed Selection to Identify a Potent Neutralizing Macrocyclic Peptide for SARS-CoV‑2

by J. Trae Hampton, Tyler J. Lalonde, Jeffery M. Tharp, Yadagiri Kurra, Yugendar R. Alugubelli, Christopher M. Roundy, Gabriel L. Hamer, Shiqing Xu, and Wenshe Ray Liu

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ACS Chemical Biology
DOI: 10.1021/acschembio.2c00565
05 Dec 14:14

Mark Levin

Mark Levin

My favorite thing about my lab group is how funny they are (aside from being fantastic and creative chemists, that is)! The memes on our group twitter page are not my doing … My favorite name reaction is the Beckmann Rearrangement. Single-atom skeletal editing traces back to carbonyl rearrangements, and you can't beat a reaction that gave us Azithromycin and Nylon …” Find out more about Mark Levin in his Introducing … Profile.


05 Dec 10:34

Catalytic asymmetric α C(sp3)–H addition of benzylamines to aldehydes

by Chengkang Hou

Nature Catalysis, Published online: 28 November 2022; doi:10.1038/s41929-022-00875-3

Carbonyl catalysis is mainly limited to strongly activated primary amines. Now, a chiral bifunctional pyridoxal organocatalyst is developed that enables the activation of the inert α C(sp3)–H bond of NH2-unprotected benzylamines affording chiral β-aminoalcohols with high diastereo- and enantioselectivities.
04 Dec 14:57

Using enzymes to tame nitrogen-centred radicals for enantioselective hydroamination

by Yuxuan Ye

Nature Chemistry, Published online: 14 November 2022; doi:10.1038/s41557-022-01083-z

Expanding the biocatalysis toolbox for C–N bond formation is of great value. Now, a biocatalytic amination strategy using a new-to-nature mechanism involving nitrogen-centred radicals has been developed. The transformations are enabled by synergistic photoenzymatic catalysis, providing intra- and intermolecular hydroamination products with high yields and levels of enantioselectivity.
01 Dec 13:45

[ASAP] Phenanthroline Catalysis in Stereoselective 1,2-cis Glycosylations

by Jiayi Li and Hien M. Nguyen

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.2c00636
01 Dec 11:35

[ASAP] Mechanism of Action of Flavin-Dependent Halogenases

by Rhys D. Barker, Yuqi Yu, Leonardo De Maria, Linus O. Johannissen, and Nigel S. Scrutton

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ACS Catalysis
DOI: 10.1021/acscatal.2c05231
29 Nov 17:37

Halogenation of the 3-position of pyridines through Zincke imine intermediates

by Benjamin T. Boyle, Jeffrey N. Levy, Louis de Lescure, Robert S. Paton, Andrew McNally
Science, Volume 378, Issue 6621, Page 773-779, November 2022.
29 Nov 14:06

Radical and ionic meta-C–H functionalization of pyridines, quinolines, and isoquinolines

by Hui Cao, Qiang Cheng, Armido Studer
Science, Volume 378, Issue 6621, Page 779-785, November 2022.
29 Nov 07:52

[ASAP] Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

by G. Logan Bartholomew, Filippo Carpaneto, and Richmond Sarpong
LongLarf

isolable but not isolated
sounds like a passive aggressive reply to a reviwer comment laughing

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c10746
28 Nov 14:05

[ASAP] Noncatalyzed Reduction of Nitriles to Primary Amines with Ammonia Borane

by Man Ding, Jiarui Chang, Jia-Xue Mao, Jie Zhang, and Xuenian Chen
LongLarf

Et2O 120 °C

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.2c01727
28 Nov 14:03

[ASAP] Design of Single-Atom Catalysts and Tracking Their Fate Using Operando and Advanced X‑ray Spectroscopic Tools

by Bidyut Bikash Sarma, Florian Maurer, Dmitry E. Doronkin, and Jan-Dierk Grunwaldt

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Chemical Reviews
DOI: 10.1021/acs.chemrev.2c00495
28 Nov 14:02

[ASAP] Genetically Encoded Phosphine Ligand for Metalloprotein Design

by Hua-Zhen Duan, Cheng Hu, Yue-Lin Li, Shi-Hao Wang, Yan Xia, Xiaohong Liu, Jiangyun Wang, and Yong-Xiang Chen

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09683
23 Nov 15:15

Bioconjugation via Hetero‐Selective Clamping of Two Different Amines with ortho‐Phthalaldehyde

by Xin Chu, Bo Li, Hao-Yang Liu, Xiaowei Sun, Xiaochen Yang, Gang He, Chuanzheng Zhou, Weimin Xuan, Shu-Lin Liu, Gong Chen
Bioconjugation via Hetero-Selective Clamping of Two Different Amines with ortho-Phthalaldehyde

Simple ortho-phthalaldehyde (OPA) reagent enables a facile and broadly applicable bioconjugation strategy via hetero-selective clamping of two different endogenous amino handles such as ϵ-NH2 of lysine and α-NH2 of α-amino acids without any pre-functionalization.


Abstract

Amino groups are common in both natural and synthetic compounds and offer a very attractive class of endogenous handles for bioconjugation. However, the ability to differentiate two types of amino groups and join them with high hetero-selectivity and efficiency in a complex setting remains elusive. Herein, we report a new method for bioconjugation via one-pot chemoselective clamping of two different amine nucleophiles using a simple ortho-phthalaldehyde (OPA) reagent. Various α-amino acids, aryl amines, and secondary amines can be crosslinked to the ϵ-amino side chain of lysine on peptides or proteins with high efficiency and hetero-selectivity. This method offers a simple and powerful means to crosslink small molecule drugs, imaging probes, peptides, proteins, carbohydrates, and even virus particles without any pre-functionalization.

23 Nov 11:02

[ASAP] Carboxylic Acids as Adaptive Functional Groups in Metallaphotoredox Catalysis

by Sebastian B. Beil, Tiffany Q. Chen, Nicholas E. Intermaggio, and David W. C. MacMillan

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.2c00607
22 Nov 11:38

[ASAP] Radicals as Exceptional Electron-Withdrawing Groups: Nucleophilic Aromatic Substitution of Halophenols Via Homolysis-Enabled Electronic Activation

by Nick Y. Shin, Elaine Tsui, Adam Reinhold, Gregory D. Scholes, Matthew J. Bird, and Robert R. Knowles

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c10296
16 Nov 16:41

[ASAP] Enantioselective Synthesis of Quaternary Oxindoles: Desymmetrizing Staudinger–Aza-Wittig Reaction Enabled by a Bespoke HypPhos Oxide Catalyst

by Changmin Xie, Jacob Kim, Binh Khanh Mai, Shixuan Cao, Rong Ye, Xin-Yi Wang, Peng Liu, and Ohyun Kwon

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09421
16 Nov 13:07

[ASAP] Racemic Synthesis of a Key 1,4-Dihydro‑2H‑spiro[isoquinoline-3,4′-piperidin]-3′-ol Building Block

by David A. Candito, Theodore A. Martinot, Jing Su, Josep Saurí, Yu-hong Lam, Leo A. Joyce, Steven M. Silverman, David L. Sloman, Matthew L. Maddess, and Michelle R. Machacek
LongLarf

piperidines maaaan

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Organic Process Research & Development
DOI: 10.1021/acs.oprd.2c00121
16 Nov 13:06

[ASAP] π‑Stacked Ion Pairs: Tightly Associated Charged Porphyrins in Ordered Arrangement Enabling Radical-Pair Formation

by Hiroki Tanaka, Yoichi Kobayashi, Ko Furukawa, Yoshinori Okayasu, Shigehisa Akine, Nobuhiro Yasuda, and Hiromitsu Maeda

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09589
16 Nov 13:06

[ASAP] Metal–Ligand Role Reversal: Hydride-Transfer Catalysis by a Functional Phosphorus Ligand with a Spectator Metal

by Quinton J. Bruch, Akira Tanushi, Peter Müller, and Alexander T. Radosevich

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c10200
16 Nov 10:32

[ASAP] Catalytic Vilsmeier–Haack Reactions for C1-Deuterated Formylation of Indoles

by Jing Xue, Yu-Shan Zhang, Zhen Huan, Jin-Dong Yang, and Jin-Pei Cheng

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The Journal of Organic Chemistry
DOI: 10.1021/acs.joc.2c02085