Shared posts

24 Nov 07:31

[ASAP] Overcoming Photochemical Limitations in Metallaphotoredox Catalysis: Red-Light-Driven C–N Cross-Coupling

by Samantha L. Goldschmid, Nicholas Eng Soon Tay, Candice L. Joe, Brendan C. Lainhart, Trevor C. Sherwood, Eric M. Simmons, Melda Sezen-Edmonds, and Tomislav Rovis
MRV

Two photon

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09745
21 Nov 17:16

[ASAP] Cyclopropenium Ions in Catalysis

by Rebecca M. Wilson and Tristan H. Lambert

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.2c00546
21 Nov 17:14

[ASAP] Emerging Trends in Cross-Coupling: Twelve-Electron-Based L1Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications

by Sharbil J. Firsan, Vilvanathan Sivakumar, and Thomas J. Colacot
MRV

K

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Chemical Reviews
DOI: 10.1021/acs.chemrev.2c00204
21 Nov 17:12

Intermolecular dearomative [4 + 2] cycloaddition of naphthalenes via visible-light energy-transfer-catalysis

Chem. Sci., 2022, 13,12503-12510
DOI: 10.1039/D2SC04005K, Edge Article
Open Access Open Access
Pramod Rai, Kakoli Maji, Sayan K. Jana, Biplab Maji
Constructing 3D molecular scaffolds from aromatic hydrocarbons is challenging. Herein, we report dearomative [4 + 2] cycloaddition reaction of naphthalenes via visible-light EnT catalysis which overcomes issues of unfavorable thermodynamics, low yields, and selectivity.
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21 Nov 09:27

Recent advances in the Nickel‐catalysed electrochemical coupling reactions with a focus on the type of bond formed

by Jisna Jose, Elizabeth J. Diana, U. S. Kanchana, Thomas V Mathew

Despite being around for many decades, electrochemical metal catalysis has recently widened the realm of electrochemical synthesis by merging sustainable electrosynthesis and tremendous metal catalysis. Nickel can be used efficiently in electrochemical metal-catalysed reactions owing to its inexpensive nature, high reactivity towards less reactive electrophiles and unique single electron transfer (SET) catalytic cycle. This review covers the recent advances in nickel-catalysed electrochemical coupling reactions from 2017 to 2022, with a focus on different reactions that forge C-C or C-heteroatom bonds.

19 Nov 14:23

Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes

MRV

Enantioselective Ugi / Ugi-azide

15 Nov 14:52

[ASAP] Shining Visible Light on Reductive Elimination: Acridine–Pd-Catalyzed Cross-Coupling of Aryl Halides with Carboxylic Acids

by Naoyuki Toriumi, Tomonori Inoue, and Nobuharu Iwasawa
MRV

a lire !

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09318
14 Nov 13:38

Palladium‐Catalyzed [6+2] Double Allene Annulation for Benzazocines Synthesis

by Haibo Xu, Shengming Ma
MRV

cycloaddition

An efficient double allene protocol for the formation of benzazocines has been developed. The reaction constitutes a highly regioselective palladium-catalyzed formal [6+2] annulation of allenyl benzoxazinanones with terminal allenes forming the challenging 8-membered cycles. Decent yields and excellent regioselectivity have been observed under mild conditions with a remarkable Z -stereoselectivity for the exo-cyclic C=C bonds. The synthetic potentials of benzazocine products have been demonstrated.

13 Nov 11:48

Nickel‐Catalyzed Site‐Selective Intermolecular C(sp3)−H Amidation

by Jinhong Chen, Hao Wang, Craig S. Day, Ruben Martin
Nickel-Catalyzed Site-Selective Intermolecular C(sp3)−H Amidation

A Ni-catalyzed site-selective intermolecular C(sp3)−H amidation has been developed. This protocol is characterized by its mild conditions, broad substrate scope, and excellent chemo- and site-selectivity, thus unlocking a complementary technique to conventional C(sp3)−N bond-forming reactions for accessing amine architectures from simple building blocks.


Abstract

A nickel-catalyzed site-selective intermolecular amidation of saturated C(sp3)−H bonds is reported. This mild protocol exhibits a predictable reactivity pattern to incorporate amide functions at C(sp3)−H sites adjacent to nitrogen and oxygen atoms in either cyclic or acyclic frameworks, thus offering a complementary reactivity profile to existing oxidative-type processes or metal-catalyzed C(sp3)−N bond-forming reactions operating via two-electron manifolds.

08 Nov 10:53

[ASAP] Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes

by Toranosuke Iida, Junichiro Kanazawa, Tadafumi Matsunaga, Kazunori Miyamoto, Keiichi Hirano, and Masanobu Uchiyama

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c09733
07 Nov 15:56

Excited-State Palladium-Catalyzed α-Selective C1-Ketonylation

by Gaoyuan Zhao, Upasana Mukherjee, Lin Zhou, Jaclyn N. Mauro, Yue Wu, Peng Liu & Ming-Yu Ngai1Department of Chemistry, Institute of Chemical Biology and Drug Discovery, State University of New York at Stony Brook, Stony Brook, New York 117942Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 152603Department of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, Pennsylvania 15260
CCS Chemistry, Ahead of Print.
17 Oct 20:16

A broadly applicable quantitative relative reactivity model for nucleophilic aromatic substitution (SNAr) using simple descriptors

Chem. Sci., 2022, 13,12681-12695
DOI: 10.1039/D2SC04041G, Edge Article
Open Access Open Access
Jingru Lu, Irina Paci, David C. Leitch
A model for SNAr reactivity is reported, built from relative rate data obtained by competition studies. Based only on molecular descriptors of the electrophile, the model predicts relative reactivity and site selectivity for many complex substrates.
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10 Oct 10:17

Oxidative Cleavage of Alkenes by Photosensitized Nitroarenes

by Tuhin Patra, Thomas Wirth
Oxidative Cleavage of Alkenes by Photosensitized Nitroarenes

This article highlights the recent seminal findings on the possibility to use photoexcited nitroarenes as modular and easily dosable reagents which can mimic the reactivity of ozonolysis for the oxidative conversion of alkenyl bonds into carbonyl groups in a highly selective fashion.


Abstract

Oxidative cleavage of alkenes into carbonyl molecules mainly relies on either ozonolysis or Lemieux-Johnson oxidation involving high valent transition metal oxides. Safety, technical concerns and highly oxidizing conditions of both these procedures limited their adoption in streamlined synthesis. Like ozone, photosensitized nitroarenes can deliver similar types of [3+2] cycloaddition products with alkenes through biradical formation and the resulting “N-doped” ozonides can safely be converted to the corresponding carbonyl compounds through hydrolysis. The high prevalence of nitroarenes with diverse electronic and steric profiles combined with the mild oxidizing power allow to modulate site-selectivity and tolerate highly sensitive functional groups ideal for application in complex molecular setup.

02 Sep 08:59

[ASAP] Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters

by Jadab Majhi, Roshan K. Dhungana, Ángel Rentería-Gómez, Mohammed Sharique, Longbo Li, Weizhe Dong, Osvaldo Gutierrez, and Gary A. Molander

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c07170
02 Sep 08:58

[ASAP] Visible-Light Photocatalyzed peri-(3 + 2) Cycloadditions of Quinolines

by Peter Bellotti, Torben Rogge, Fritz Paulus, Ranjini Laskar, Nils Rendel, Jiajia Ma, K. N. Houk, and Frank Glorius
MRV

!

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c05687
02 Sep 08:52

[ASAP] Hydroamination of Unactivated Alkenes with Aliphatic Azides

by Si-Ming Jia, Yi-Hang Huang, Zhan-Lin Wang, Fang-Xu Fan, Bo-Han Fan, Hao-Xiang Sun, Hao Wang, and Fei Wang

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c07643
02 Sep 08:50

[ASAP] Ligand Development for Copper-Catalyzed Enantioconvergent Radical Cross-Coupling of Racemic Alkyl Halides

by Xiao-Yang Dong, Zhong-Liang Li, Qiang-Shuai Gu, and Xin-Yuan Liu

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c06718
25 Aug 09:08

[ASAP] Catalytic Lewis Base Additive Enables Selective Copper-Catalyzed Borylative α‑C–H Allylation of Alicyclic Amines

by Borja Pérez-Saavedra, Álvaro Velasco-Rubio, Eva Rivera-Chao, Jesús A. Varela, Carlos Saá, and Martín Fañanás-Mastral

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c07969
18 Aug 07:19

[ASAP] Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes

by Dan E. Wise, Emma S. Gogarnoiu, Alana D. Duke, Joshua M. Paolillo, Taylor L. Vacala, Waseem A. Hussain, and Marvin Parasram

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c05648
02 Jul 12:56

[ASAP] Synthesis of β‑Polychlorinated Alkynes Enabled by Copper-Catalyzed Multicomponent Reaction

by Qiuzhu Wang, Mengning Wang, Qianhui Wu, Mengtao Ma, and Binlin Zhao

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Organic Letters
DOI: 10.1021/acs.orglett.2c01755
28 Jun 08:12

Progress in Convergent Paired Electrolysis

by Sheng Zhang, Michael Findlater
Progress in Convergent Paired Electrolysis

Recent progress on convergent paired electrolysis has been summarized in this concept article. Four strategies based upon metal catalysis, persistent radical effects, microfluidic chemistry, and alternating current electrolysis are discussed in relation to their underlying mechanisms.


Abstract

Convergent paired electrolysis combines both anodic and cathodic reactions simultaneously in an electrochemical transformation. It provides a highly energy-efficient and divergent approach to conventionally challenging and useful structures. However, the physical separation of the two half-electrode reactions makes it extremely difficult to couple the intermediates arising from the two electrodes. In this concept article, four strategies used in convergent paired electrolysis will be discussed from the perspective of the reaction mechanism: a) metal-catalyzed convergent paired electrolysis, b) convergent paired electrolysis enabled by persistent radical effects, c) microfluidic chemistry applied to convergent paired electrolysis, and d) alternating current electrolysis.

28 Jun 08:09

[ASAP] A Pyridine-Based Donor–Acceptor Molecule: A Highly Reactive Organophotocatalyst That Enables the Reductive Cleavage of C–Br Bonds through Halogen Bonding

by Natsuki Kato, Takeshi Nanjo, and Yoshiji Takemoto

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ACS Catalysis
DOI: 10.1021/acscatal.2c02067
17 Jun 12:10

Iron-catalyzed ring-opening of cyclic carboxylic acids enabled by photoinduced ligand-to-metal charge transfer

Green Chem., 2022, 24,5553-5558
DOI: 10.1039/D2GC01738E, Paper
Jia-Lin Tu, Han Gao, Mengqi Luo, Lulu Zhao, Chao Yang, Lin Guo, Wujiong Xia
A decarboxylative ring-opening reaction of cyclic tertiary carboxylic acids via an iron-catalyzed photoinduced ligand-to-metal charge transfer (LMCT) process is herein reported.
The content of this RSS Feed (c) The Royal Society of Chemistry
15 Jun 13:54

[ASAP] Regio- and Stereoselective Electrochemical Alkylation of Morita–Baylis–Hillman Adducts

by Giulio Bertuzzi, Giada Ombrosi, and Marco Bandini

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Organic Letters
DOI: 10.1021/acs.orglett.2c01529
03 Jun 09:57

[ASAP] Organocatalyzed Cross-Nucleophile Couplings: Umpolung of Catalytic Enamines

by Nomaan M. Rezayee, Johannes N. Lamhauge, and Karl Anker Jrgensen

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Accounts of Chemical Research
DOI: 10.1021/acs.accounts.2c00149
14 May 15:33

[ASAP] Photoinduced Transition-Metal-Free Chan–Evans–Lam-Type Coupling: Dual Photoexcitation Mode with Halide Anion Effect

by Zijun Zhou, Jeonguk Kweon, Hoimin Jung, Dongwook Kim, Sangwon Seo, and Sukbok Chang

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c03343
09 May 17:23

Copper‐Catalyzed Radical Enantioselective Carbo‐Esterification of Styrenes Enabled by a Perfluoroalkylated‐PyBox Ligand

by Zaicheng Nie, Mong-Feng Chiou, Jinfeng Cui, Yanjie Qu, Xiaotao Zhu, Wujun Jian, Haigen Xiong, Yajun Li, Hongli Bao
MRV

.....

Copper-Catalyzed Radical Enantioselective Carbo-Esterification of Styrenes Enabled by a Perfluoroalkylated-PyBox Ligand

The radical enantioselective carbo-esterification of styrenes enabled by a newly developed perfluoroalkylated-PyBox ligand and copper catalysis is reported. Mechanistic studies reveal that this reaction is a rare example of an efficient ligand-decelerated system, in which the ligand decelerates the reaction, but the reaction is still efficient with reduced amounts of ligand.


Abstract

Chiral lactones are found in many natural products. The reaction of simple alkenes with iodoacetic acid is a powerful method to build lactones, but the enantioselective version of this reaction has not been implemented to date. Herein, we report the efficient catalytic radical enantioselective carbo-esterification of styrenes enabled by a newly developed CuI-perfluoroalkylated PyBox system. Simple styrenes have been converted to useful chiral lactones, whose synthetic applications are showcased. Mechanistic studies reveal that this reaction is a rare example of an efficient ligand-decelerated system, in which the ligand decelerates the reaction, but the reaction is still efficient with reduced amounts of ligand. This uncommon catalytic system may inspire further consideration of the effect of ligands in asymmetric catalysis.

09 May 15:38

Para‐Fluorination of Anilides Using Electrochemically Generated Hypervalent Iodoarenes

by Michael Berger, Marola S. Lenhard, Siegfried R Waldvogel
MRV

electrochemical fluorination

Para-Fluorination of Anilides Using Electrochemically Generated Hypervalent Iodoarenes

An electrochemical transformation for the selective para-fluorination of anilides is presented. Herein, anodically generated ArIF2 mediates the conversion of a variety of 20 different anilides in up to 86 % yield. The sustainable and easy to conduct protocol in an ionic-liquid / dicholoromethane mixture represents a promising alternative to conventional reagent mediated synthesis protocol.


Abstract

The para-selective fluorination reaction of anilides using electrochemically generated hypervalent ArIF2 is reported, with Et3N ⋅ 5HF serving as fluoride source and as supporting electrolyte. This electrochemical reaction is characterized by a simple set-up, easy scalability and affords a broad variety of fluorinated anilides from easily accessible anilides in good yields up to 86 %.

09 May 15:36

Catalytic asymmetric Tsuji–Trost α−benzylation reaction of N-unprotected amino acids and benzyl alcohol derivatives

MRV

:nice:

09 May 08:23

[ASAP] Organocatalytic Asymmetric Dearomatizing Hetero-Diels–Alder Reaction of Nonactivated Arenes

by Kai Li, Shengli Huang, Tianyu Liu, Shiqi Jia, and Hailong Yan
MRV

smile

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Journal of the American Chemical Society
DOI: 10.1021/jacs.2c01106