Category: 78782-17-9

The author of 《Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling》 were Xu, Meng-Yu; Jiang, Wei-Tao; Li, Ying; Xu, Qing-Hao; Zhou, Qiao-Lan; Yang, Shuo; Xiao, Bin. And the article was published in Journal of the American Chemical Society in 2019. Recommanded Product: Bis[(pinacolato)boryl]methane The author mentioned the following in the article:

Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp3)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp2)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp3)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp3)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analog. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an “”SE2(open) Inv”” pathway, which is consistent with Hiyama’s previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis. The experimental part of the paper was very detailed, including the reaction process of Bis[(pinacolato)boryl]methane(cas: 78782-17-9Recommanded Product: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Recommanded Product: Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2018,Lee, Yeosan; Park, Jinyoung; Cho, Seung Hwan published 《Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem-Diborylalkanes by an Asymmetric Allylic Substitution》.Angewandte Chemie, International Edition published the findings.Name: Bis[(pinacolato)boryl]methane The information in the text is summarized as follows:

Authors report the successful generation of (diborylmethyl)zinc(II) species by transmetalation between isolable (diborylmethyl)lithium and zinc(II) halide (X = Br, Cl) and their application in the synthesis of enantioenriched gem-diborylalkanes bearing a stereogenic center at the β-position of the diboryl groups by an asym. allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem-diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem-diborylalkanes provides access to a diverse set of valuable chiral building blocks. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Name: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Name: Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Lee, Yeosan; Baek, Seung-yeol; Park, Jinyoung; Kim, Seoung-Tae; Tussupbayev, Samat; Kim, Jeongho; Baik, Mu-Hyun; Cho, Seung Hwan published 《Chemoselective Coupling of 1,1-Bis[(pinacolato)boryl]alkanes for the Transition-Metal-Free Borylation of Aryl and Vinyl Halides: A Combined Experimental and Theoretical Investigation》.Journal of the American Chemical Society published the findings.Recommanded Product: Bis[(pinacolato)boryl]methane The information in the text is summarized as follows:

A new transition-metal-free borylation of aryl and vinyl halides using 1,1-bis[(pinacolato)boryl]alkanes as boron sources is described. In this transformation one of the boron groups from 1,1-bis[(pinacolato)boryl]alkanes is selectively transferred to aryl and vinyl halides in the presence of sodium tert-butoxide as the only activator to form organoboronate esters. Under the developed borylation conditions, a broad range of organohalides are borylated with excellent chemoselectivity and functional group compatibility, thus offering a rare example of a transition-metal-free borylation protocol. Exptl. and theor. studies have been performed to elucidate the reaction mechanism, revealing the unusual formation of Lewis acid/base adduct between organohalides and α-borylcarbanion, generated in situ from the reaction of 1,1-bis[(pinacolato)boryl]alkanes with an alkoxide base, to facilitate the borylation reactions. In the experiment, the researchers used many compounds, for example, Bis[(pinacolato)boryl]methane(cas: 78782-17-9Recommanded Product: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Recommanded Product: Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《ZnMe2-Mediated, Direct Alkylation of Electron-Deficient N-Heteroarenes with 1,1-Diborylalkanes: Scope and Mechanism》 was written by Jo, Woohyun; Baek, Seung-yeol; Hwang, Chiwon; Heo, Joon; Baik, Mu-Hyun; Cho, Seung Hwan. Formula: C13H26B2O4This research focused onzinc promoted regioselective alkylation pyridine quinoline diborylalkane. The article conveys some information:

The regioselective, direct alkylation of electron-deficient N-heteroarenes is, in principle, a powerful and efficient way of accessing alkylated N-heteroarenes that are important core structures of many biol. active compounds and pharmaceutical agents. Herein, we report a ZnMe2-promoted, direct C2- or C4-selective primary and secondary alkylation of pyridines and quinolines using 1,1-diborylalkanes as alkylation sources. While substituted pyridines and quinolines exclusively afford C2-alkylated products, simple pyridine delivers C4-alkylated pyridine with excellent regioselectivity. The reaction scope is remarkably broad, and a range of C2- or C4-alkylated electron-deficient N-heteroarenes are obtained in good yields. Exptl. and computational mechanistic studies imply that ZnMe2 serves not only as an activator of 1,1-diborylalkanes to generate (α-borylalkyl)methylalkoxy zincate, which acts as a Lewis acid to bind to the nitrogen atom of the heterocycles and controls the regioselectivity, but also as an oxidant for rearomatizing the dihydro-N-heteroarene intermediates to release the product.Bis[(pinacolato)boryl]methane(cas: 78782-17-9Formula: C13H26B2O4) was used in this study.

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Formula: C13H26B2O4 Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Fei, Zhuping; Han, Yang; Gann, Eliot; Hodsden, Thomas; Chesman, Anthony S. R.; McNeill, Christopher R.; Anthopoulos, Thomas D.; Heeney, Martin published 《Alkylated Selenophene-Based Ladder-Type Monomers via a Facile Route for High-Performance Thin-Film Transistor Applications》.Journal of the American Chemical Society published the findings.Name: Bis[(pinacolato)boryl]methane The information in the text is summarized as follows:

We report the synthesis of two new selenophene-containing ladder-type monomers, cyclopentadiselenophene (CPDS) and indacenodiselenophene (IDSe), via a 2-fold and 4-fold Pd-catalyzed coupling with a 1,1-diborylmethane derivative Copolymers with benzothiadiazole were prepared in high yield by Suzuki polymerization to afford materials which exhibited excellent solubility in a range of nonchlorinated solvents. The CPDS copolymer exhibited a band gap of just 1.18 eV, which is among the lowest reported for donor-acceptor polymers. Thin-film transistors were fabricated using environmentally benign, nonchlorinated solvents, with the CPDS and IDSe copolymers exhibiting hole mobility up to 0.15 and 6.4 cm2 V-1 s-1, resp. This high performance was achieved without the undesirable peak in mobility often observed at low gate voltages due to parasitic contact resistance. The results came from multiple reactions, including the reaction of Bis[(pinacolato)boryl]methane(cas: 78782-17-9Name: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Name: Bis[(pinacolato)boryl]methane Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

《Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity》 was published in European Journal of Organic Chemistry in 2020. These research results belong to Ivon, Yevhen M.; Kuchkovska, Yuliya O.; Voitenko, Zoya V.; Grygorenko, Oleksandr O.. Name: Bis[(pinacolato)boryl]methane The article mentions the following:

A protocol for the preparation of α-boryl-α-bromoketones from alkenyl MIDA boronates was developed and applied to functionalized aliphatic derivatives The reaction sequence included regioselective hydroxybromination of olefin moiety, followed by oxidation of alc. group with Dess-Martin periodinane. The target trifunctional boronate-containing derivatives were obtained in up to 94% yield over two steps starting from alkenyl MIDA boronates. In some cases, functional groups present in the substrate participated in the bromohydroxylation step via intramol. nucleophilic attack at the bromonium cation leading to cyclic products. Addnl., the reactivity of aliphatic α-boryl-α-bromoketones was illustrated by nucleophilic substitution at the α-C atom and heterocyclization reactions. In the experiment, the researchers used many compounds, for example, Bis[(pinacolato)boryl]methane(cas: 78782-17-9Name: Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Name: Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of Bis[(pinacolato)boryl]methaneIn 2017 ,《Development of neighboring electrophilic activation of active center in catalytic reactions via organometallic intermediates》 appeared in Bulletin of the Chemical Society of Japan. The author of the article were Endo, Kohei. The article conveys some information:

A review. Strategies for electrophilic activation by neighboring atoms should contribute to the development of novel catalytic performance in organic reactions. Neighboring electron-withdrawing Lewis acidic atoms can change the character of mol. catalysts, which might be more electrophilic toward inactive electron-rich mols. In this context, the development of carbene intermediates, diborylmethane derivatives, and multinuclear catalysts has realized efficient transformations. The use of cyclopropenes can generate electrophilic carbenoid intermediates in the presence of a Ag-catalyst, the reaction of which with an organozinc reagent gives allylzinc intermediates. The subsequent allylation reaction of other electrophiles takes place in situ as a 3-components coupling reaction. The novel reactivity of diborylmethane derivatives shows the generation of borate intermediates under ambient conditions, which can take part in the Suzuki Miyaura cross-coupling reaction. The mono-coupling reaction occurs exclusively without di-coupling reaction to give alkylboronates. The stereoselective synthesis of tetrasubstituted alkenylboronates was successful via the deprotonation of diborylalkanes, subsequent nucleophilic attack to ketones, and syn-elimination. The development of multinuclear catalysts using phosphorous ligands bearing protic moieties has realized efficient stereoselective 1,4-addition reaction of organozinc and organoaluminum reagents, where the creation of chiral quaternary stereogenic centers using acyclic enones is notable. After reading the article, we found that the author used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Reference of Bis[(pinacolato)boryl]methane)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds.Reference of Bis[(pinacolato)boryl]methane Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2017,Miura, Tomoya; Nakahashi, Junki; Murakami, Masahiro published 《Enantioselective Synthesis of (E)-δ-Boryl-Substituted anti-Homoallylic Alcohols Using Palladium and a Chiral Phosphoric Acid》.Angewandte Chemie, International Edition published the findings.Electric Literature of C13H26B2O4 The information in the text is summarized as follows:

(E)-δ-Boryl-substituted anti-homoallylic alcs. were synthesized in a highly diastereo- and enantioselective manner from 1,1-di(boryl)alk-3-enes and aldehydes. Mechanistically, the reaction consists of 1: Pd-catalyzed double-bond transposition of the 1,1-di(boryl)alk-3-enes to 1,1-di(boryl)alk-2-enes, 2: chiral phosphoric acid catalyzed allylation of aldehydes, and 3: Pd-catalyzed geometrical isomerization from the Z to E isomer. As a result, the configurations of two chiral centers and one double bond are all controlled with high selectivity in a single reaction vessel. In the experiment, the researchers used Bis[(pinacolato)boryl]methane(cas: 78782-17-9Electric Literature of C13H26B2O4)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.Electric Literature of C13H26B2O4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In 2019,Angewandte Chemie, International Edition included an article by Jang, Won Jun; Yun, Jaesook. Application of 78782-17-9. The article was titled 《Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis》. The information in the text is summarized as follows:

The authors report the catalytic enantioselective conjugate addition of a borylalkyl Cu nucleophile generated in situ from a 1,1-diborylmethane derivative to α,β-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)-Cu catalyst, this method facilitated the enantioselective incorporation of a CH2Bpin moiety at the β-position of the diesters to yield β-chiral alkyl boronates in up to 86% yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C-B bond. The experimental process involved the reaction of Bis[(pinacolato)boryl]methane(cas: 78782-17-9Application of 78782-17-9)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds have been a cornerstone of synthetic transformations for decades. Areas such as boron-containing catalysts, metalate chemistry, photoredox methods, and boryl anions have brought significant new developments in understanding and provided new reactivity upon.Application of 78782-17-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Roy, Satyajit; Das, Sandip Kumar; Khatua, Hillol; Das, Subrata; Singh, Krishna Nand; Chattopadhyay, Buddhadeb published an article in 2021. The article was titled 《Iron-Catalyzed Radical Activation Mechanism for Denitrogenative Rearrangement Over C(sp3)-H Amination》, and you may find the article in Angewandte Chemie, International Edition.COA of Formula: C13H26B2O4 The information in the text is summarized as follows:

An iron-catalyzed denitrogenative rearrangement of 1,2,3,4-tetrazole is developed over the competitive C(sp3)-H amination. This catalytic rearrangement reaction follows an unprecedented metalloradical activation mechanism. Employing the developed method, a wide number of complex-N-heterocyclic product classes have been accessed. The synthetic utility of this radical activation method is showcased with the short synthesis of a bioactive mol. Collectively, this discovery underlines the progress of radical activation strategy that should find wide application in the perspective of medicinal chem., drug discovery and natural product synthesis research. The experimental part of the paper was very detailed, including the reaction process of Bis[(pinacolato)boryl]methane(cas: 78782-17-9COA of Formula: C13H26B2O4)

Bis[(pinacolato)boryl]methane(cas: 78782-17-9) belongs to organoboron compounds. Organoboron compounds are versatile intermediates and as such are some of the most important classes of reagents in modern organic chemistry. This stems from their ease of preparation combined with their ability to undergo a broad range of chemical transformations.COA of Formula: C13H26B2O4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts