Category: 5344-90-1

Das, Siuli; Sinha, Suman; Samanta, Deepannita; Mondal, Rakesh; Chakraborty, Gargi; Brandao, Paula; Paul, Nanda D. published the artcile< Metal-Ligand Cooperative Approach To Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3H)-ones under Mild Aerobic Conditions>, Category: alcohols-buliding-blocks, the main research area is quinoline preparation cooperative metal ligand catalyzed dehydrogenative functionalization alc; quinazolinone preparation cooperative metal ligand catalyzed dehydrogenative functionalization alc.

A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcs. to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) (L1,2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.

Journal of Organic Chemistry published new progress about Acetophenones Role: RCT (Reactant), RACT (Reactant or Reagent). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhan, Bing; Li, Zhi-Ming; Hou, Xiu-Feng published the artcile< Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects>, COA of Formula: C7H9NO, the main research area is potential energy surface iridacycle complex catalyzed methylation aniline DFT; bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand preparation catalyst; crystal structure bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand; mol structure bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand; isotope effect iridium carbene complex catalyzed methylation aniline.

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significantly increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogs (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones and nitro compounds with various functional groups, can be well tolerated. Mechanistic studies and DFT calculation highlights the significance of bimetallic centers cooperativity.

Organometallics published new progress about Anilines Role: SPN (Synthetic Preparation), PREP (Preparation) (N-Me). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, COA of Formula: C7H9NO.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Wang, Zheng; Lin, Qing; Ma, Ning; Liu, Song; Han, Mingyang; Yan, Xiuli; Liu, Qingbin; Solan, Gregory A.; Sun, Wen-Hua published the artcile< Direct synthesis of ring-fused quinolines and pyridines catalyzed by NNHY-ligated manganese complexes (Y = NR2 or SR)>, Computed Properties of 5344-90-1, the main research area is cationic manganese complex preparation; fused quinoline pyridine preparation green chem; gamma amino secondary alc ketone coupling cyclization.

Four cationic manganese(I) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (where NNH is a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alc. with a ketone or secondary alc.; NNHS-ligated Mn-4 proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and exptl. evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclic N-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.

Catalysis Science & Technology published new progress about Amino alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Computed Properties of 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Genc, Sertac; Arslan, Burcu; Gulcemal, Suleyman; Gunnaz, Salih; Cetinkaya, Bekir; Gulcemal, Derya published the artcile< Iridium(I)-Catalyzed C-C and C-N Bond Formation Reactions via the Borrowing Hydrogen Strategy>, Computed Properties of 5344-90-1, the main research area is secondary aminobenzyl alc alkylation cyclization iridium catalyst.

Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the β-alkylation of secondary alcs. with primary alcs. and acceptorless dehydrogenative cyclization of 2-aminobenzyl alc. with ketones through a borrowing hydrogen pathway. The β-alkylated alcs., including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of the catalyst with a catalytic amount of NaOH or KOH under the air atm., liberating water (and H2 in the case of quinoline synthesis) as the sole byproduct. Notably, this system demonstrated turnover numbers of 940,000 (for β-alkylation of secondary alcs. with primary alcs. by using down to 0.0001 mol % = 1 ppm of the catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alc. with ketones).

Journal of Organic Chemistry published new progress about Alkylation (β-, of secondary alcs. with primary alcs.). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Computed Properties of 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Tabasi, Nihal S.; Genc, Sertac; Gulcemal, Derya published the artcile< Tuning the selectivity in iridium-catalyzed acceptorless dehydrogenative coupling of primary alcohols>, HPLC of Formula: 5344-90-1, the main research area is carboxylic acid ester alkali carboxylate preparation iridium catalyst; primary alc dehydrogenation; alc preparation homo cross alkylation.

An acceptorless dehydrogenative coupling of primary alcs. to carboxylic acids/carboxylates, esters, and Guerbet alcs. (via both homo- and cross-β-alkylation of the alcs.) in the presence of an N-heterocyclic carbene iridium(I) catalyst was developed under aerobic conditions. The product selectivity can be easily tuned among the products with a single catalyst through simple modification of the reaction conditions, such as the catalyst and base amounts, the choice of base, and the reaction temperature

Organic & Biomolecular Chemistry published new progress about Alkylation. 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, HPLC of Formula: 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Guo, Bin; Yu, Tian-Qi; Li, Hong-Xi; Zhang, Shi-Qi; Braunstein, Pierre; Young, David J.; Li, Hai-Yan; Lang, Jian-Ping published the artcile< Phosphine Ligand-Free Ruthenium Complexes as Efficient Catalysts for the Synthesis of Quinolines and Pyridines by Acceptorless Dehydrogenative Coupling Reactions>, Formula: C7H9NO, the main research area is quinoline preparation green chem; aminobenzyl secondary alc dehydrogenative coupling ruthenium complex catalyst; pyridine preparation green chem; amino secondary alc dehydrogenative coupling ruthenium complex catalyst.

A series of phosphine-free Ru(III)/Ru(II) complexes of NH functionalized N N N pincer ligands exhibit excellent activity for acceptorless dehydrogenative coupling (ADC) of secondary alcs. RCH(OH)CH2R1 [R = Ph, thiophen-2-yl, Et, etc.; R1 = H, Me, Et, n-Pr; RR1 = -(CH2)4-] and bicyclo[2.2.1]heptan-2-ol with 2-aminobenzyl 2-NH2-R3C6H3CH(R2)OH [R2 = H, Me; R3 = H, 5-Me, 4-Cl] or γ-amino alcs. R4CH(NH2)(CH2)2OH (R4 = Ph, Me) to quinolines I (R5 = H, 6-Me, 7-Cl), 1,2,3,4-tetrahydro-1,4-methanoacridine and pyridines II. Ru(III) complexes [LRuCl3] III (R6 = R7 = R8 = H, R9 = Cl; R6 = H, R7 = R8 = Me, R9 = Cl; R6 = R7 = H, R8 = Ph, R9 = Cl, etc.) were obtained by refluxing RuCl3.xH2O with the corresponding ligand in EtOH. Five Ru(II) complexes [LRu(DMSO-κS)Cl2] III [R9 = S(CH3)2(O)] were formed by reducing the corresponding Ru(III) complex in refluxing EtOH. The latter complexes could also be prepared directly by refluxing Ru(DMSO)4Cl2 with the corresponding ligand in EtOH. These Ru(III) and Ru(II) complexes, especially III exhibited high catalytic efficiency and broad functional group tolerance in ADC reactions of secondary alcs. with 2-aminobenzyl or γ-amino alcs. to quinolines I and pyridines II. A detail mechanistic study indicated that the Ru(III) complex III (R9 = Cl) was reduced into the Ru(II) species III (R9 = S(CH3)2(O)), which was the active catalytic center for ADC via a Ru-H/N-H bifunctional outer-sphere mechanism. This protocol provides a reliable, atom-economical and environmentally benign procedure for C-N and C-C bond formation.

ChemCatChem published new progress about Amino alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Formula: C7H9NO.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhan, Bing; Li, Zhi-Ming; Hou, Xiu-Feng published the artcile< Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects>, COA of Formula: C7H9NO, the main research area is potential energy surface iridacycle complex catalyzed methylation aniline DFT; bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand preparation catalyst; crystal structure bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand; mol structure bimetallic biscarbene iridium complex containing arylbenzooxazolyl ligand; isotope effect iridium carbene complex catalyzed methylation aniline.

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significantly increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogs (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones and nitro compounds with various functional groups, can be well tolerated. Mechanistic studies and DFT calculation highlights the significance of bimetallic centers cooperativity.

Organometallics published new progress about Anilines Role: SPN (Synthetic Preparation), PREP (Preparation) (N-Me). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, COA of Formula: C7H9NO.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Wang, Zheng; Lin, Qing; Ma, Ning; Liu, Song; Han, Mingyang; Yan, Xiuli; Liu, Qingbin; Solan, Gregory A.; Sun, Wen-Hua published the artcile< Direct synthesis of ring-fused quinolines and pyridines catalyzed by NNHY-ligated manganese complexes (Y = NR2 or SR)>, Computed Properties of 5344-90-1, the main research area is cationic manganese complex preparation; fused quinoline pyridine preparation green chem; gamma amino secondary alc ketone coupling cyclization.

Four cationic manganese(I) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (where NNH is a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alc. with a ketone or secondary alc.; NNHS-ligated Mn-4 proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and exptl. evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclic N-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%.

Catalysis Science & Technology published new progress about Amino alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Computed Properties of 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Genc, Sertac; Arslan, Burcu; Gulcemal, Suleyman; Gunnaz, Salih; Cetinkaya, Bekir; Gulcemal, Derya published the artcile< Iridium(I)-Catalyzed C-C and C-N Bond Formation Reactions via the Borrowing Hydrogen Strategy>, Computed Properties of 5344-90-1, the main research area is secondary aminobenzyl alc alkylation cyclization iridium catalyst.

Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the β-alkylation of secondary alcs. with primary alcs. and acceptorless dehydrogenative cyclization of 2-aminobenzyl alc. with ketones through a borrowing hydrogen pathway. The β-alkylated alcs., including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of the catalyst with a catalytic amount of NaOH or KOH under the air atm., liberating water (and H2 in the case of quinoline synthesis) as the sole byproduct. Notably, this system demonstrated turnover numbers of 940,000 (for β-alkylation of secondary alcs. with primary alcs. by using down to 0.0001 mol % = 1 ppm of the catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alc. with ketones).

Journal of Organic Chemistry published new progress about Alkylation (β-, of secondary alcs. with primary alcs.). 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, Computed Properties of 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Tabasi, Nihal S.; Genc, Sertac; Gulcemal, Derya published the artcile< Tuning the selectivity in iridium-catalyzed acceptorless dehydrogenative coupling of primary alcohols>, HPLC of Formula: 5344-90-1, the main research area is carboxylic acid ester alkali carboxylate preparation iridium catalyst; primary alc dehydrogenation; alc preparation homo cross alkylation.

An acceptorless dehydrogenative coupling of primary alcs. to carboxylic acids/carboxylates, esters, and Guerbet alcs. (via both homo- and cross-β-alkylation of the alcs.) in the presence of an N-heterocyclic carbene iridium(I) catalyst was developed under aerobic conditions. The product selectivity can be easily tuned among the products with a single catalyst through simple modification of the reaction conditions, such as the catalyst and base amounts, the choice of base, and the reaction temperature

Organic & Biomolecular Chemistry published new progress about Alkylation. 5344-90-1 belongs to class alcohols-buliding-blocks, and the molecular formula is C7H9NO, HPLC of Formula: 5344-90-1.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts