Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

Wang, Christy; Sperry, Jonathan

doi:10.1021/jo300330u

Cited by 26 publications

(18 citation statements)

References 24 publications

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“…When H 2 O 2 and NaOH were added to the polymerization mixture, the pinacol boronate terminal of PPP was converted to a hydroxyl group (Entry 3) . The MALDI‐TOF mass spectrum showed small peaks of PPP with OH and H end groups, which might stem from deboronation with base (Figure S6, Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…When H 2 O 2 and NaOH were added to the polymerization mixture, the pinacol boronate terminal of PPP was converted to a hydroxyl group (Entry 3). [ 22 ] The MALDI-TOF mass spectrum showed small peaks of PPP with OH and H end groups, which might stem from deboronation with base ( Figure S6, Supporting Information). Conversion of the pinacol boronate terminal to bromine by addition of N -bromosuccinimide (NBS) to the polymerization mixture failed, but isolated PPP was reacted with NBS at 60 °C for 24 h to yield PPP with bromine at both ends (Entry 4).…”

Section: Chain-end Functionalizationmentioning

confidence: 99%

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Alternating Intramolecular and Intermolecular Catalyst‐Transfer Suzuki–Miyaura Condensation Polymerization: Synthesis of Boronate‐Terminated π‐Conjugated Polymers Using Excess Dibromo Monomers

Nojima

Kosaka

Kato

et al. 2015

Macromol. Rapid Commun.

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The Suzuki-Miyaura coupling polymerization of dibromoarene 1 and arylenediboronic acid (ester) 2 with a Pd catalyst having a high propensity for intramolecular catalyst transfer is reported. The polymerization of excess 1 with 2 affords high-molecular-weight π-conjugated polymer having boronic acid (ester) moieties at both ends, contrary to Flory's principle. This unstoichiometric polycondensation behavior is accounted for by intramolecular transfer of the Pd catalyst on 1. In the polymerization of 1 and 2 having different aryl residues, high-molecular-weight polymer is obtained when the stronger donor aromatic is used as the dibromo monomer and the weaker donor or acceptor aromatic is used as diboronic acid (ester) monomer. The pinacol boronate moieties at both ends of the obtained poly(p-phenylene) (PPP) can be converted to benzoic acid ester, hydroxyl group, and bromine. Furthermore, the reaction of the pinacol boronate-terminated PPP with poly(3-hexylthiophene) (P3HT) having bromine at one end yields a triblock copolymer of P3HT-b-PPP-b-P3HT.

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Section: Resultsmentioning

confidence: 99%

Section: Chain-end Functionalizationmentioning

confidence: 99%

Alternating Intramolecular and Intermolecular Catalyst‐Transfer Suzuki–Miyaura Condensation Polymerization: Synthesis of Boronate‐Terminated π‐Conjugated Polymers Using Excess Dibromo Monomers

Nojima

Kosaka

Kato

et al. 2015

Macromol. Rapid Commun.

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“…Additional complex molecules have now been prepared by related uses of arylboronate intermediates generated by C−H bond borylation. 190,191 …”

Section: Applications Of C−h Bond Functionalization To the Synthesis mentioning

confidence: 99%

Evolution of C–H Bond Functionalization from Methane to Methodology

2015

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This Perspective presents the fundamental principles, the elementary reactions, the initial catalytic systems, and the contemporary catalysts that have converted C−H bond functionalization from a curiosity to a reality for synthetic chemists. Many classes of elementary reactions involving transition-metal complexes cleave C−H bonds at typically unreactive positions. These reactions, coupled with a separate or simultaneous functionalization process lead to products containing new C−C, C−N, and C−O bonds. Such reactions were initially studied for the conversion of light alkanes to liquid products, but they have been used (and commercialized in some cases) most often for the synthesis of the more complex structures of natural products, medicinally active compounds, and aromatic materials. Such a change in direction of research in C−H bond functionalization is remarkable because the reactions must occur at an unactivated C−H bond over functional groups that are more reactive than the C−H bond toward classical reagents. The scope of reactions that form C−C bonds or install functionality at an unactivated C−H bond will be presented, and the potential future utility of these reactions will be discussed.

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“…The propensity of DDQ to act as oxidant was utilized by Li, Gao and co-workers to develop DDQ/NaNO 2 as effective catalyst for the oxidation of alcohols 108 using molecular oxygen as the terminal oxidant at room temperature (Scheme 96). [70] The protocol was however compatible with allylic, propargylic, cinnamyl and electron-rich benzylic alcohols only and was inefficient for electron-deficient benzylic alcohols or failed with aliphatic alcohols. It is proposed that NaNO 2 releases NO in the presence of AcOH, which is transformed into NO 2 by dioxygen while DDQ was the catalytic oxidant, oxidizing alcohols to the desired products.…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Applications of Sodium Nitrite in Organic Synthesis

Mukhopadhyay

Batra

2019

Eur J Org Chem

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Sodium nitrite (NaNO2) is a cheap inorganic reagent that has wide applications in synthetic organic chemistry. The Sandmeyer reaction for transforming amines into diazo derivatives and nitration, including the oxidative ones, are well known and globally used in several industrial processes too. Sodium nitrite is also used in the Nef reaction and Abidi transformation besides several other important reactions. The ability of NaNO2 to produce NO·, NO2, and N2O4 under oxidative conditions has considerably assisted in the discovery of its newer applications. Strikingly, this has resulted in remarkable development in reactions involving NaNO2 as either catalyst or reagent, and this review is an attempt to assimilate them. Wherever possible the mechanistic details associated with the reported reaction/transformation is provided.

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Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones

Cited by 26 publications

References 24 publications

Alternating Intramolecular and Intermolecular Catalyst‐Transfer Suzuki–Miyaura Condensation Polymerization: Synthesis of Boronate‐Terminated π‐Conjugated Polymers Using Excess Dibromo Monomers

Alternating Intramolecular and Intermolecular Catalyst‐Transfer Suzuki–Miyaura Condensation Polymerization: Synthesis of Boronate‐Terminated π‐Conjugated Polymers Using Excess Dibromo Monomers

Evolution of C–H Bond Functionalization from Methane to Methodology

Applications of Sodium Nitrite in Organic Synthesis

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