Arylboronic Acid Chemistry under Electrospray Conditions

Wang, Lifang; Dai, Chong; Burroughs, Sarah; Wang, Siming Liu; Wang, Binghe

doi:10.1002/chem.201204290

Cited by 13 publications

(15 citation statements)

References 39 publications

(7 reference statements)

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“…Indeed, this product no longer exhibits the isotopic splitting characteristic of boron, suggesting the elimination of B(OH) from the product. 1 H, 11 B, and 13 C nuclear magnetic resonance (NMR) spectroscopy ( Figures S4, S5, and S7) confirms these ESI-MS results. Specifically, the para product shows a single 11 B resonance with a chemical shift consistent with typical BAs, whereas the ortho product shows no 11 B signal whatsoever.…”

supporting

confidence: 72%

Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

Jones

Wheeler

et al. 2015

Tetrahedron Letters

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Boronic acids (BAs) are useful functionalities for programmable stimuli-responsive chemistry, due to their Lewis acid character with pK a values tunable across physiological pH and their reversible binding to saccharides, catechols, and other compounds bearing 1,2-diol moieties. 1 In addition, BAs have emerged as valuable reagents and intermediates in important synthetic pathways, such as Suzuki cross-coupling reactions, 1 and as selective enzyme inhibitors, exemplified by the commercial success of the anti-cancer drug Bortezomib. 2 Over the last decade, researchers have studied a variety of BA-modified peptides, focusing on the inhibitory properties of the BA or the use of the BA as a functional element in peptide self-assembly. 3 For example, our group has recently reported the reversible selfassembly behavior of a BA dipeptide, controllable by pH, ionic strength, and the addition of polyols. 3s

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supporting

confidence: 72%

Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

Jones

Wheeler

et al. 2015

Tetrahedron Letters

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“…[58] In the second cross-coupling reaction, 4Ј-bromoterpyridine (4) was attached to 3 by using [Pd(dppf)Cl 2 ] as catalyst, Rb 2 CO 3 as base, and dioxane with 2 % water as a solvent, giving a 60 % yield of the metalloligand 5-(2,7-di-tert-butyl-9,9-dimethyl-5-terpyridyl-4Ј-ylxanthen-4-yl)-10,20-dimesitylporphyrinatozinc (5). Sect.…”

Section: Synthesis and Characterization Of Precursor Moleculesmentioning

confidence: 99%

“…One interesting feature to note is that the mass spectroscopic analysis of 3a is hampered by a fast reaction with the solvent methanol in the ESI-MS. [58,60,61] Recrystallization from a dcm/methanol solution yielded single crystals of 7·1.75CH 3 OH·0.5H 2 O suitable for X-ray crystallography ( Figure 2). [58] In the second cross-coupling reaction, 4Ј-bromoterpyridine (4) was attached to 3 by using [Pd(dppf)Cl 2 ] as catalyst, Rb 2 CO 3 as base, and dioxane with 2 % water as a solvent, giving a 60 % yield of the metalloligand 5-(2,7-di-tert-butyl-9,9-dimethyl-5-terpyridyl-4Ј-ylxanthen-4-yl)-10,20-dimesitylporphyrinatozinc (5).…”

Section: Synthesis and Characterization Of Precursor Moleculesmentioning

confidence: 99%

High‐Yielding Synthesis of a Hetero‐Pacman Compound and the Characterization of Intermediates and Side‐Products

et al. 2014

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Through an optimized synthetic procedure, metalloligand 5, which features a hetero-Pacman scaffold comprising a porphyrin and a terpyridine moiety, has been assembled by a double Suzuki reaction. In a subsequent step, a rutheniumbipyridine fragment was introduced at the terpyridine coordination site of metalloligand 5 to form complex 6, which was fully characterized and its potential application in water oxidation catalysis tested. A number of side-products were iso-[a] Institute Scheme 1. Synthesis of compound 6 (mes = mesityl). Reagents and conditions: a) i. BuLi, B(OMe) 3 ; ii. H + /H 2 O; b) 2, [Pd(dppf)Cl 2 ], Rb 2 CO 3 , thf; c) CHCl 3 /MeOH; d) 4, [Pd(dppf)Cl 2 ], Rb 2 CO 3 , dioxane/water; e) i. [Ru(CH 3 CN) 2 (bpy)Cl 2 ], acetone; ii. NH 4 PF 6 /H 2 O.

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“…Our lab has had a long-standing interest in boronic acid chemistry, exploring its applications in sensing, 13 catalysis, 14 drug design, 15 and imaging 16 as well as its behavior in mass spectrometry. 17 It is well known that a Lewis base/nucleophile in a 1,5-relationship with an arylboronic acid can donate its lone pair electrons to the boron open shell. This has been shown with amino and hydroxyl groups.…”

mentioning

confidence: 99%