Dichloroborane–dioxane: an exceptional reagent for the preparation of alkenyl- and alkylboronic acids

Josyula, Kanth V. B.; Gao, Peng; Hewitt, Chris

doi:10.1016/j.tetlet.2003.08.086

Cited by 19 publications

(8 citation statements)

References 31 publications

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“…Except for phenylboronic acid (2a) and benzene-1,4-diboronic acid (2b), all other boronic acids (i.e., 2c-h) were synthesized following reported procedures. [24,25] General Procedure for the Synthesis of Complexes 4: To a mixture of Boc-protected bis-cyclen chlorotriazene 1 (100 mg, 0.1 mmol) and Pd(PPh 3 ) 4 (10 mg, 0.012 mmol, 12 mol-%) in DME was added required aryl boronic acid 2 (1.5 equiv. of monoboronic acid and 0.5 equiv.…”

Section: Methodsmentioning

confidence: 99%

Rigid Luminescent Bis‐Zinc(II)–Bis‐Cyclen Complexes for the Detection of Phosphate Anions and Non‐Covalent Protein Labeling in Aqueous Solution

et al. 2011

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A series of water‐soluble bis‐ and tetrakis‐ZnII–cyclen complexes with rigid structures was prepared to enhance the carboxylate and phosphate ion binding response in contrast to analogues with less‐confined molecular structures. Boc‐protected 6‐chloro‐1,3,5‐triazine–bis‐cyclen was coupled to different aryl and alkyl moieties in moderate to high yields and subsequently converted into the corresponding bis‐ or tetrakis‐ZnII–cyclen complexes. The bis‐ZnII–cyclen moiety is known for its affinity to anions. Depending on the arene substituent some of the synthesized synthetic receptors are luminescent. They were studied by absorption and emission spectroscopy for their response to the presence of phosphate anions of biological relevance in buffered aqueous solution at neutral pH and for their affinity to the genetically encodable oligoaspartate and glutamate sequences (D4 and E4 tag) recently introduced. The rigid structures of the compounds enhance the electronic coupling between the metal complex binding site and the reporter dye. This leads to an increased anion binding response in homogeneous aqueous solution.

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Section: Methodsmentioning

confidence: 99%

Rigid Luminescent Bis‐Zinc(II)–Bis‐Cyclen Complexes for the Detection of Phosphate Anions and Non‐Covalent Protein Labeling in Aqueous Solution

et al. 2011

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“…36,37 Phenethylboronic acids are available from styrenes via hydroboration with dichloroborane, followed by aqueous hydrolysis. 38…”

Section: N-arylethylation With Phenethyl Boron Compoundsmentioning

confidence: 99%

Methods for Arylethylation of Amines and Heteroarenes

Bracher

2018

SynOpen

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“…Chiral 3,3′-disubstituted binaphthols were synthesized using procedures from a previous report. 1 Volatile alkenylboronates (Table 3, entries 1-4 and 6-10) were prepared from the corresponding alkenylboronic acid [2][3][4][5][6] by treatment with 1:2.4 methanol/CHCl 3 in the presence of molecular sieves 3Å (Dean-Stark apparatus, reflux for 48 hours) and were distilled prior to use. Non-volatile boronates (Table 3, entry 5) were generated from alkenylboronic acids in the presence of 1:2 MeOH/CH 2 Cl 2 and molecular sieves 3Å (room temperature S 3 for 48 hours) and were used without further purification.…”

Section: General Experimentalmentioning

confidence: 99%