Tag: 300-400

In 2022,Chen, Yuqing; Yan, Huaipu; Liao, Qian; Zhang, Dandan; Lin, Shuangjie; Hao, Erjun; Murtaza, Rukhsana; Li, Chenchen; Wu, Chao; Duan, Chunying; Shi, Lei published an article in Angewandte Chemie, International Edition. The title of the article was 《Synthesis of Homoallylic Amines by Radical Allylation of Imines with Butadiene under Photoredox Catalysis》.Name: tert-Butyl 4-iodopiperidine-1-carboxylate The author mentioned the following in the article:

A conceptually different radical-radical cross-coupling strategy for the synthesis of a homoallyl amines RCH2CH=CHCH2CH(NHR1)(R2) (R = oxetan-3-yl, 3-methylbut-3-en-1-yl, 2-(tert-butoxy)-2-oxoethyl, etc.; R1 = 4-fluorophenyl, 2,4,6-trimethylphenyl, naphthalen-2-yl, etc.; R2 = thiophen-2-yl, 3,4-dimethoxyphenyl, 4-[methoxy(oxo)methyl]phenyl, etc.) between an α-amino alkyl radical and a transient allylic radical have been reported. This metal-free method provided a novel approach for the synthesis of homoallylic amines (>80 examples) from readily available materials with excellent regioselectivity and exceptional broad functional group compatibility. The results came from multiple reactions, including the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Name: 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.Name: tert-Butyl 4-iodopiperidine-1-carboxylate

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

In 2019,Journal of the American Chemical Society included an article by Hazra, Avijit; Chen, Jason; Lalic, Gojko. Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate. The article was titled 《Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes》. The information in the text is summarized as follows:

The authors have developed a method for stereospecific synthesis of E-alkenes from terminal alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov selectivity. The authors demonstrate the broad scope of the reaction, which can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl chlorides, anilines, and a wide range of nitrogen-containing heteroaromatic compounds Mechanistic studies provide evidence that the copper catalyst activates the alkyne by hydrocupration, which controls both the regio- and diastereoselectivity of the overall reaction. The nickel catalyst activates the alkyl iodide and promotes cross coupling with the alkenyl copper intermediate. In addition to this study using tert-Butyl 4-iodopiperidine-1-carboxylate, there are many other studies that have used tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate) 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.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate

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

In 2018,Chen, Yi-Hung; Grassl, Simon; Knochel, Paul published 《Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates》.Angewandte Chemie, International Edition published the findings.Category: iodides-buliding-blocks The information in the text is summarized as follows:

Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25° within 2-4 h in the presence of 2.5-5.0% CoCl2·2LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56% overall yield by using this cobalt-catalyzed amination as the key step. In the experiment, the researchers used 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. 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.Category: iodides-buliding-blocks

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

In 2018,Cheng, Li-Jie; Islam, Shahidul M.; Mankad, Neal P. published 《Synthesis of Allylic Alcohols via Cu-Catalyzed Hydrocarbonylative Coupling of Alkynes with Alkyl Halides》.Journal of the American Chemical Society published the findings.Reference of tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

We have developed a modular procedure to synthesize allylic alcs. from tertiary, secondary, and primary alkyl halides and alkynes via a Cu-catalyzed hydrocarbonylative coupling and 1,2-reduction tandem sequence. The use of tertiary alkyl halides as electrophiles was found to enable the synthesis of various allylic alcs. bearing α-quaternary carbon centers in good yield with high 1,2-reduction selectivity. Mechanistic studies that suggested a different pathway was operative with tertiary alkyl halides compared with primary and secondary alkyl halides for generating the key copper(III) oxidative adduct. For tertiary electrophiles, an acyl halide likely forms via radical atom transfer carbonylation. The preference for 1,2-reduction over 1,4-reduction of α,β-unsaturated ketones bearing tertiary substituents was rationalized using d. functional theory transition state anal. On the basis of this computational model, the coupling method was extended to primary and secondary alkyl iodide electrophiles by using internal alkynes with aryl substituents, providing trisubstituted allylic alcs. in high yield with good regioselectivity. The experimental process involved the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Reference of tert-Butyl 4-iodopiperidine-1-carboxylate)

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.Reference of tert-Butyl 4-iodopiperidine-1-carboxylate

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

Synthetic Route of C6H2ClF3INOn June 1, 2020, Xiao, Li-Jun; Hong, Kai; Luo, Fan; Hu, Liang; Ewing, William R.; Yeung, Kap-Sun; Yu, Jin-Quan published an article in Angewandte Chemie, International Edition. The article was 《PdII-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group》. The article mentions the following:

In the presence of Pd(OAc)2, 3-nitro-5-trifluoromethyl-2-pyridone, and D-valine as a transient directing group reagent, cyclobutyl ketones such as I (R = H) underwent regioselective, diastereoselective, and enantioselective arylation with aryl iodides R1I (R1 = 4-MeO2CC6H4, 4-O2NC6H4, 4-MeCOC6H4, 4-NCC6H4, 4-F3CC6H4, 3-O2NC6H4, 3-PhCOC6H4, 3,4,5-F3C6H2, 3,5-Br2C6H3, 3-Br-5-ClC6H3, 4-Me-3-O2NC6H3, 2-Br-5-FC6H3, 6-F-3-pyridinyl, 2-F3C-4-pyridinyl, 6-Cl-5-F3C-3-pyridinyl, 6-Br-3-pyridinyl, 2,6-F2-4-pyridinyl, 2,6-F2-3-pyridinyl, 2,6-Cl2-4-pyridinyl, 5-acetyl-2-thienyl) to yield arylcyclobutyl ketones such as I (R = 4-MeO2CC6H4, 4-O2NC6H4, 4-MeCOC6H4, 4-NCC6H4, 4-F3CC6H4, 3-O2NC6H4, 3-PhCOC6H4, 3,4,5-F3C6H2, 3,5-Br2C6H3, 3-Br-5-ClC6H3, 4-Me-3-O2NC6H3, 2-Br-5-FC6H3, 6-F-3-pyridinyl, 2-F3C-4-pyridinyl, 6-Cl-5-F3C-3-pyridinyl, 6-Br-3-pyridinyl, 2,6-F2-4-pyridinyl, 2,6-F2-3-pyridinyl, 2,6-Cl2-4-pyridinyl, 5-acetyl-2-thienyl). In the presence of either L-valine as a transient directing group reagent or when silver trifluoroacetate, acetate, carbonate, or oxide were used as bases, enantiomeric arylcyclobutyl ketones were formed. A sequential diarylation was performed to yield diastereomeric diarylcyclobutyl ketones enantioselectively. In the experiment, the researchers used 2-Chloro-5-iodo-3-(trifluoromethyl)pyridine(cas: 887707-25-7Synthetic Route of C6H2ClF3IN)

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.Synthetic Route of C6H2ClF3IN

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

In 2022,Chen, Yuqing; Yan, Huaipu; Liao, Qian; Zhang, Dandan; Lin, Shuangjie; Hao, Erjun; Murtaza, Rukhsana; Li, Chenchen; Wu, Chao; Duan, Chunying; Shi, Lei published an article in Angewandte Chemie, International Edition. The title of the article was 《Synthesis of Homoallylic Amines by Radical Allylation of Imines with Butadiene under Photoredox Catalysis》.Name: tert-Butyl 4-iodopiperidine-1-carboxylate The author mentioned the following in the article:

A conceptually different radical-radical cross-coupling strategy for the synthesis of a homoallyl amines RCH2CH=CHCH2CH(NHR1)(R2) (R = oxetan-3-yl, 3-methylbut-3-en-1-yl, 2-(tert-butoxy)-2-oxoethyl, etc.; R1 = 4-fluorophenyl, 2,4,6-trimethylphenyl, naphthalen-2-yl, etc.; R2 = thiophen-2-yl, 3,4-dimethoxyphenyl, 4-[methoxy(oxo)methyl]phenyl, etc.) between an α-amino alkyl radical and a transient allylic radical have been reported. This metal-free method provided a novel approach for the synthesis of homoallylic amines (>80 examples) from readily available materials with excellent regioselectivity and exceptional broad functional group compatibility. The results came from multiple reactions, including the reaction of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Name: 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.Name: tert-Butyl 4-iodopiperidine-1-carboxylate

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

《Synthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling》 was published in Angewandte Chemie, International Edition in 2020. These research results belong to Nugent, Jeremy; Shire, Bethany R.; Caputo, Dimitri F. J.; Pickford, Helena D.; Nightingale, Frank; Houlsby, Ian T. T.; Mousseau, James J.; Anderson, Edward A.. Category: iodides-buliding-blocks The article mentions the following:

1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Access to all-carbon disubstituted BCPs via cross-coupling has to date been limited to use of the BCP as the organometallic component, which restricts scope due to the harsh conditions typically required for the synthesis of metalated BCPs. Here the authors report a general method to access 1,3-C-disubstituted BCPs from 1-iodo-bicyclo[1.1.1]pentanes (iodo-BCPs) by direct iron-catalyzed cross-coupling with aryl and heteroaryl Grignard reagents. This chem. represents the first general use of iodo-BCPs as electrophiles in cross-coupling, and the first Kumada coupling of tertiary iodides. Benefiting from short reaction times, mild conditions, and broad scope of the coupling partners, it enables the synthesis of a wide range of 1,3-C-disubstituted BCPs including various drug analogs. The experimental process involved the reaction of 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. 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.Category: iodides-buliding-blocks

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

In 2016,Anka-Lufford, Lukiana L.; Huihui, Kierra M. M.; Gower, Nicholas J.; Ackerman, Laura K. G.; Weix, Daniel J. published 《Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents》.Chemistry – A European Journal published the findings.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, the authors demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity. 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: 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.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate

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

《Cu-Catalyzed Hydrocarbonylative C-C Coupling of Terminal Alkynes with Alkyl Iodides》 was written by Cheng, Li-Jie; Mankad, Neal P.. Recommanded Product: 301673-14-3This research focused onunsym dialkyl ketone regioselective synthesis; copper catalyzed hydrocarbonylative coupling terminal alkyne unactivated alkyl iodide. The article conveys some information:

A Cu-catalyzed hydrocarbonylative C-C coupling of terminal alkynes with unactivated alkyl iodides has been developed, enabling highly chemo- and regioselective synthesis of unsym. dialkyl ketones. A variety of functional groups are tolerated, and both primary and secondary alkyl iodides react well. An autotandem sequence of two Cu-catalyzed processes is proposed: first hydrocarbonylative coupling of the alkyne and the alkyl iodide, followed by reduction of the intermediate unsaturated ketone to the saturated product. Mechanistic experiments indicate that an alkenylcopper intermediate activates the alkyl iodide by single electron transfer to enable a radical carbonylation pathway. In the experiment, the researchers used many compounds, for example, 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. 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: 301673-14-3

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

Application of 301673-14-3In 2022 ,《Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis》 appeared in Journal of the American Chemical Society. The author of the article were Jia, Xue-Gong; Yao, Qi-Wei; Shu, Xing-Zhong. The article conveys some information:

Asym. cross-electrophile difunctionalization of tethered alkenes has become a powerful tool for the production of chiral cyclic scaffolds; however, the current studies all focus on carbocyclization reactions. Herein, an N-cyclization-alkylation reaction and showcase on the potential of heterocyclization for accessing new enantioenriched cyclic architectures is reported. This work establishes a new approach for enantioselective aza-Heck cyclization/cross-coupling sequence, which remains a long-standing unsolved challenge for the synthetic community. The reaction proceeds with primary, secondary, and a few tertiary alkyl iodides, and the use of newly defined ligands gave highly enantioenriched pyrrolines with improved mol. diversity under mild conditions. The presence of imine functionality allows for further structural variations. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Application of 301673-14-3)

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.Application of 301673-14-3

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