Tag: 300-400

Tripathy, Alisha Rani; A, Rizwana Rahmathulla; Kumar, Amit; Yatham, Veera Reddy published an article in 2022. The article was titled 《Photocatalyzed alkylative cyclization of 2-isocyanobiphenyls with unactivated alkyl iodides》, and you may find the article in Organic & Biomolecular Chemistry.Formula: C10H18INO2 The information in the text is summarized as follows:

Herein, the first photocatalyzed radical cascade cyclization of 2-isocyanobiaryls with unactivated alkyl iodides was reported for the synthesis of 6-alkyl substituted phenanthridines I [R = n-Pr, t-Bu, cyclohexyl, etc.; R1 = H, Cl; R2 = H, 8-Et, 9-Me, etc.]. This simple protocol operated under mild reaction conditions and affords 6-alkyl phenanthridines in good yields. To elucidate the reaction mechanism, Stern-Volmer quenching studies were carried out and these studies revealed that the photocatalyst is not directly involved in a single electron transfer process with the alkyl iodide.tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Formula: C10H18INO2) was used in this study.

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs. Oceanic alkyl iodides are believed to be the principal source of atmospheric iodine.Formula: C10H18INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Cheng, Li-Jie; Zhao, Siling; Mankad, Neal P. published their research in Angewandte Chemie, International Edition in 2021. The article was titled 《One-Step Synthesis of Acylboron Compounds via Copper-Catalyzed Carbonylative Borylation of Alkyl Halides**》.Category: iodides-buliding-blocks The article contains the following contents:

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides was developed, enabling efficient synthesis of aliphatic K acyltrifluoroborates (KATs) in high yields by treating the in situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary, and tertiary alkyl halides are all applicable. This method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated K acyltrifluoroborates in a 1-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin. In the experimental materials used by the author, we found tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Category: iodides-buliding-blocks)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Category: iodides-buliding-blocks

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Zhang, Fang-Lin; Hong, Kai; Li, Tuan-Jie; Park, Hojoon; Yu, Jin-Quan published an article on January 15 ,2016. The article was titled 《Functionalization of C(sp3)-H bonds using a transient directing group》, and you may find the article in Science (Washington, DC, United States).Recommanded Product: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine The information in the text is summarized as follows:

Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Recommanded Product: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine) was used in this study.

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Recommanded Product: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Chen, Yan-Qiao; Wang, Zhen; Wu, Yongwei; Wisniewski, Steven R.; Qiao, Jennifer X.; Ewing, William R.; Eastgate, Martin D.; Yu, Jin-Quan published their research in Journal of the American Chemical Society on December 26 ,2018. The article was titled 《Overcoming the Limitations of γ- and δ-C-H Arylation of Amines through Ligand Development》.Recommanded Product: 887707-25-7 The article contains the following contents:

L,X-Type transient directing groups (TDGs) based on a reversible imine linkage have emerged as broadly useful tools for C-H activation of ketones and free amines. However, competitive binding interactions among multiple reaction components (TDG itself, substrate, and substrate-TDG adduct) with the palladium catalyst often lead to the formation of multiple unreactive complexes, rendering ligand development extremely challenging. Herein, we report the finding of versatile 2-pyridone ligands that addresses these problems and significantly improves the γ-methylene arylation of alkyl amines, extending the coupling partners to a wide range of medicinally important heteroaryl iodides and even previously unreactive heteroaryl bromides. The combination of an appropriate transient directing group and pyridone ligand has also enabled the δ-arylation of alkyl amines. Notably, our transient directing group design reveals the importance of matching the size of the Pd-chelation with different transient directing groups and the size of palladacycles generated from γ- and δ-C-H bonds: TDGs that coordinate with Pd(II) to form a six-membered chelate are selective toward γ-C-H bonds, whereas TDGs that coordinate with Pd(II) via a five-membered chelate tend to activate δ-C-H bonds. These findings provide an avenue for developing protecting group free and selective C-H functionalization using the transient directing group strategy. In the part of experimental materials, we found many familiar compounds, such as 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Recommanded Product: 887707-25-7)

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Recommanded Product: 887707-25-7

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Formula: C10H18INO2In 2019 ,《Catalyst Free Reductive Coupling of Aromatic and Aliphatic Nitro Compounds with Organohalides》 was published in Angewandte Chemie, International Edition. The article was written by Rauser, Marian; Eckert, Raphael; Gerbershagen, Max; Niggemann, Meike. The article contains the following contents:

A rare reductive coupling of nitro compounds with organohalides has been realized. The reaction is initiated by a partial reduction of the nitro group to a nitrenoid intermediate. Therefore, not only aromatic but also aliphatic nitro compounds are efficiently transformed into monoalkylated amines, with organohalides as the alkylating agent. Given the innate reactivity of the nitrenoid, a catalyst is not required, resulting in a high tolerance for aryl halide substituents in both starting materials. The experimental process involved the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Formula: C10H18INO2)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Formula: C10H18INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The author of 《Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters》 were Bera, Srikrishna; Hu, Xile. And the article was published in Angewandte Chemie, International Edition in 2019. Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate The author mentioned the following in the article:

Metal hydride catalyzed hydrocarbonation reactions of alkenes are an efficient approach to construct new C-C bonds from readily available alkenes. However, the regioselectivity of hydrocarbonation remains challenging to be controlled. In Ni hydride (NiH) catalyzed hydrocarbonation, linear selectivity is most often obtained because of the relative stability of the linear Ni-alkyl intermediate over its branched counterpart. Herein, the boronic pinacol ester (Bpin) group directs a Ni-catalyzed hydrocarbonation to occur at its adjacent C center, resulting in formal branch selectivity. Both alkyl and aryl halides can be used as electrophiles in this hydrocarbonation, providing access to a wide range of secondary alkyl Bpin derivatives, which are valuable building blocks in synthetic chem. The utility of the method is demonstrated by the late-stage functionalization of natural products and drug mols., the synthesis of an anticancer agent, and iterative syntheses. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2017,Nuhant, Philippe; Oderinde, Martins S.; Genovino, Julien; Juneau, Antoine; Gagne, Yohann; Allais, Christophe; Chinigo, Gary M.; Choi, Chulho; Sach, Neal W.; Bernier, Louise; Fobian, Yvette M.; Bundesmann, Mark W.; Khunte, Bhagyashree; Frenette, Mathieu; Fadeyi, Olugbeminiyi O. published 《Visible-Light-Initiated Manganese Catalysis for C-H Alkylation of Heteroarenes: Applications and Mechanistic Studies》.Angewandte Chemie, International Edition published the findings.Safety of tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

A visible-light-driven Minisci protocol that employs an inexpensive earth-abundant metal catalyst, decacarbonyldimanganese Mn2(CO)10, to generate alkyl radicals from alkyl iodides has been developed. This Minisci protocol is compatible with a wide array of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert-Bu carbamates (Boc-group), cyclobutanes, and spirocycles. The robustness of this protocol is demonstrated on the late-stage functionalization of complex nitrogen-containing drugs. Photophys. and DFT studies indicate a light-initiated chain reaction mechanism propagated by Mn(CO)5 radical. The rate-limiting step is the iodine abstraction from an alkyl iodide by Mn(CO)5 radical. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Safety of tert-Butyl 4-iodopiperidine-1-carboxylate)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Safety of tert-Butyl 4-iodopiperidine-1-carboxylate

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2018,Soulard, Valentin; Villa, Giorgio; Vollmar, Denis Patrick; Renaud, Philippe published 《Radical Deuteration with D2O: Catalysis and Mechanistic Insights》.Journal of the American Chemical Society published the findings.Recommanded Product: 301673-14-3 The information in the text is summarized as follows:

N-Dodecanethiol acts as a catalyst for the chemoselective radical deuteration of alkyl iodides with D2O initiated by dry air and Et3B. The method is compatible with a wide range of functional groups and provides the monodeuterated products in good yields and with a high level of deuterium incorporation. A revised mechanism for the deoxygenation of xanthates using alkylboranes and water (Wood deoxygenation) is proposed involving dialkylthioborinates as intermediates; n-C12H25SBEt2 is prepared and found to be a competent catalyst for radical deuteration of an alkyl iodide in the absence of thiol. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Recommanded Product: 301673-14-3)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Recommanded Product: 301673-14-3

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Ye, Ning; Wu, Bin; Zhao, Kangming; Ge, Xiaobin; Zheng, Yu; Shen, Xiaodong; Shi, Lei; Cortes-Clerget, Margery; Regnier, Morgan Louis; Parmentier, Michael; Gallou, Fabrice published their research in Chemical Communications (Cambridge, United Kingdom) in 2021. The article was titled 《Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in water via synergistic nickel and copper catalysis》.COA of Formula: C10H18INO2 The article contains the following contents:

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developed via nickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3COA of Formula: C10H18INO2)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Organic iodides are used in veterinary products (Organic Iodide Powder) as a nutritional source of iodine. In the chemical industry, alkyl iodides serve as excellent alkylating agents and, specifically, methyl iodide is used as a methylating agent in the synthesis of various pharmaceutical drugs. Oceanic alkyl iodides are believed to be the principal source of atmospheric iodine.COA of Formula: C10H18INO2

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Name: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridineOn September 12, 2018 ,《Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers》 was published in Journal of the American Chemical Society. The article was written by Green, Samantha A.; Vasquez-Cespedes, Suhelen; Shenvi, Ryan A.. The article contains the following contents:

Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chem.: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings. In the experiment, the researchers used 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Name: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine)

2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.Name: 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com