Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
Julianna M. Mouat ; Jonas K. Widness ; Daniel G. Enny , et al. ACS Catal.,2023,13(13):9018-9024. DOI: 10.1021/acscatal.3c01984 PubMed ID: 38283073
More
Abstract: Semiconductor quantum dots (QDs) offer many advantages as photocatalysts for synthetic photoredox catalysis, but no reports have explored the use of QDs with nickel catalysts for C–C bond formation. We show here that 5.7 nm CdS QDs are robust photocatalysts for photoredox-promoted cross-electrophile coupling (turnover number (TON) up to 40,000). These conditions can be utilized on a small scale (96-well plate) or adapted to flow. NMR studies show that triethanolamine (TEOA)-capped QDs are the active catalyst and that TEOA can displace native phosphonate and carboxylate ligands, demonstrating the importance of the QD surface chemistry.
Keywords: quantum dot ; nanoplatelet ; nickel ; cross-electrophile coupling ; C?C bond formation ; photochemistry
Purchased from AmBeed: 83948-53-2 ; 180695-79-8 ; 166953-64-6 ; 131379-33-4 ; 364359-05-7
CAS No. : | 180695-79-8 | MDL No. : | MFCD04115039 |
Formula : | C10H18BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | KZBWIYHDNQHMET-UHFFFAOYSA-N |
M.W : | 264.16 | Pubchem ID : | 15541517 |
Synonyms : |
|
Chemical Name : | N-Boc-4-Bromopiperidine |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P280-P301+P312-P305+P351+P338-P337+P313 | UN#: | |
Hazard Statements: | H302-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Step 1: Synthesis of 4-Bromo-piperidine-1-carboxylic acid tert-butyl ester To a suspension of 5 g (0.02 mol) of <strong>[54288-70-9]4-bromopiperidine hydrobromide</strong> salt in DCM (35 mL) are added 7.09 mL (0.04 mol) of N,N-diisopropylethyl amine dropwise at 0° C. The reaction mixture is stirred for 30 min, then a solution of 6.67 g (0.31 mol) of di-tert-butyl dicarbonate in DCM (35 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred for 18 h at room temperature, then washed with 1M aqueous HCl solution (2*30 mL) and brine (30 mL). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 6.9 g of 4-bromo-piperidine-l-carboxylic acid tert-butyl ester as a yellow oil. Yield quantitative; 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.46 (9H, s), 1.79-2.00 (2H, m), 2.00-2.16 (2H, m), 3.31 (2H, ddd, J=13.67, 7.73, 3.73 Hz), 3.68 (2H, ddd, J=13.55, 6.85, 3.65 Hz), 4.34 (1H, tt, J=7.69, 3.81 Hz) | |
100% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; | To a suspension of 5 g (0.02 mol) of Compound 29 salt in DCM (35 mL) are added 7.09 mL (0.04 mol) of N,N-diisopropylethyl amine dropwise at 0° C. The reaction mixture is stirred for 30 min, then a solution of 6.67 g (0.31 mol) of di-tert-butyl dicarbonate in DCM (35 mL) is added dropwise to the reaction mixture. The reaction mixture is stirred for 18 h at room temperature, washed with 1M aqueous HCl solution (2.x.30 mL) and brine (30 mL). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 6.9 g of Compound 30 as a yellow oil. Yield quantitative; 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 1.46 (9H, s), 1.79-2.00 (2H, m), 2.00-2.16 (2H, m), 3.31 (2H, ddd, J=13.67, 7.73, 3.73 Hz), 3.68 (2H, ddd, J=13.55, 6.85, 3.65 Hz), 4.34 (1H, tt, J=7.69, 3.81 Hz). |
98% | With triethylamine; In tetrahydrofuran; at 20℃; for 48h; | Triethylamine (2.3 mL, 16.3 mmol) and di-tert-butyl dicarbonate (1.9 g, 8.6 mmol) were added to astirred suspension of <strong>[54288-70-9]4-bromopiperidine hydrobromide</strong> (2.0 g, 8.2 mmol) in THF (40 mL). Thereaction mixture was stirred for 48 h at rt. The suspension was filtered and the filter was washedwith THF. The combined filtrate was evaporated in vacuo. Purification by flash chromatography(petroleum ether 40?60 °C/EtOAc, 95:5 v/v) afforded 19 (2.11 g, 98percent) as colourless oil |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | The tetrahydrofuran in Example 1 was replaced by the same amount of N, N-dimethylformamide, and the other procedures were the same as in Example 1,Rate 88%. (S) - (4-chlorophenyl) (2-pyridyl) -methanol 21.9 g (0.1 mol) of the formula (II)Was dissolved in 160 mL of tetrahydrofuran,41 g (0.1 mol) of sodium hydride in a mass fraction of 60% was added portionwise with stirring,Stirring for 2 hours to no bubbles,The reaction was allowed to cool under ice-coolingA solution of 26.4 g (0.1 mol) of N-t-butoxycarbonyl-4-bromopiperidine was added dropwise,After completion of the dropwise addition, the reaction was gradually warmed to room temperature with stirring for 5 hours,The reaction solution was added to 200 mL of saturated ammonium chloride solution,Stirred for 30 minutes,The reaction solution was extracted twice with 300 mL of ethyl acetate,The organic phases were combined,Dried over anhydrous sodium sulfate for 2 hours,filter,The mother liquor was evaporated to dryness to give 34.3 g of product,The product was directly subjected to the next reaction without purification,Yield 85%. |
[ 849928-26-3 ]
tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 1354000-03-5 ]
(R)-tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 169457-73-2 ]
tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate
Similarity: 0.91
[ 939793-16-5 ]
tert-Butyl 3-bromopyrrolidine-1-carboxylate
Similarity: 0.89
[ 193629-39-9 ]
N-Boc-3-(bromomethyl)piperidine
Similarity: 0.89
[ 849928-26-3 ]
tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 1354000-03-5 ]
(R)-tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 169457-73-2 ]
tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate
Similarity: 0.91
[ 939793-16-5 ]
tert-Butyl 3-bromopyrrolidine-1-carboxylate
Similarity: 0.89
[ 193629-39-9 ]
N-Boc-3-(bromomethyl)piperidine
Similarity: 0.89
[ 849928-26-3 ]
tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 1354000-03-5 ]
(R)-tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 169457-73-2 ]
tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate
Similarity: 0.91
[ 939793-16-5 ]
tert-Butyl 3-bromopyrrolidine-1-carboxylate
Similarity: 0.89
[ 193629-39-9 ]
N-Boc-3-(bromomethyl)piperidine
Similarity: 0.89
[ 849928-26-3 ]
tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 1354000-03-5 ]
(R)-tert-Butyl 3-bromopiperidine-1-carboxylate
Similarity: 0.91
[ 169457-73-2 ]
tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylate
Similarity: 0.91
[ 193629-39-9 ]
N-Boc-3-(bromomethyl)piperidine
Similarity: 0.89
[ 158407-04-6 ]
tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate
Similarity: 0.89