Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages

Christinat, Nicolas; Scopelliti, Rosario; Severin, Kay

doi:10.1002/anie.200705272

Cited by 224 publications

(110 citation statements)

References 58 publications

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“…However, the topologies we discuss can still be used to describe the underlying connectivity in a multicomponent system and indeed, multiple components may be an attractive design approach for the synthesis of some of the lower symmetry topologies. Several examples of multiple component systems, [52][53][54][55] including those with orthogonal DCC formation reactions, for example both boronate and imine formation, 50,56 have been reported.…”

Section: Enumeration Of Organic Cage Topologiesmentioning

confidence: 99%

Topological landscapes of porous organic cages

et al. 2017

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We define a nomenclature for the classification of porous organic cage molecules, enumerating the 20 most probable topologies, 12 of which have been synthetically realised to date. We then discuss the computational challenges encountered when trying to predict the most likely topological outcomes from dynamic covalent chemistry (DCC) reactions of organic building blocks. This allows us to explore the extent to which comparing the internal energies of possible reaction outcomes is successful in predicting the topology for a series of 10 different building block combinations.

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Section: Enumeration Of Organic Cage Topologiesmentioning

confidence: 99%

Topological landscapes of porous organic cages

et al. 2017

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“…Heating a solution of a mixture of 3-aminophenylboronic acid (L43) with pentaerythritol (L44), 3-chloro-4-formylpyridine (L45), and [ReBr(CO) 5 ] in THF/benzene resulted in the formation of a yellow solid 66 (Scheme 21) [173]. Analytical data for 66 were in agreement with the desired macrocyclic structure.…”

mentioning

confidence: 75%

Neutral discrete metal–organic cyclic architectures: Opportunities for structural features and properties in confined spaces

Thanasekaran

Lee

2014

Coordination Chemistry Reviews

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“…For this purpose, the boronic acid is generally converted to an ester (boronate) via condensation with an aliphatic or aromatic diol, which is then assembled to amacromolecular structure via reaction of the additional functional group attached to the B-phenyl ring [4][5][6]. In this context, 3-aminophenylboronic acid has been employed for the generation of macrocycles and cages [7][8][9][10][11]. In contrast to the analogous ester derived from pinacol [12], in this case the water adduct has been obtained, which has converted to the corresponding zwitterion and crystallized as dihydrate.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of aqua-2-(3-aminophenyl)-1,3,2-dioxaborole dihydrate, C12H12BNO3 · 2H2O

Vega¹,

Zarate²,

Tlahuext³

et al. 2010

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialFor the preparation of the compound, as olution of 3-aminophenylboronic acid monohydrate (0.250 g, 1.61 mmol) and catechol (0.177 g, 1.61 mmol) in 20 mL of asolvent mixture of methanol and benzene (1:4) was refluxed for 1hinthe presence of aD ean-Stark trap. Ap recipitate formed upon cooling was recrystallized from as olvent mixture of methanol, dichloromethane and water to give crystals suitable for X-ray diffraction analysis (m.p. 448 K). Experimental detailsHatoms were positioned geometrically and constrained using the riding-model approximationw ith d(C-H aryl )=0 .93 Å and U iso (H aryl )=1 .2 U eq (C). Hydrogen atoms bonded to O( H3, H31A, H31B, H31C, H32A, H32B and H32C) and N(H1A, H1B and H1C) were located in difference Fourier maps. One of the two hydrogen atoms in each water molecule is disordered over two positions with an occupancy factor of 0.50 (H31B and H31C for O31; H32B and H32C for O32). The disorder arises from the presence of crystallographic inversion centers in the O31···O31 and O32···O32 H-bonds. As aconsequence disorder is observed also in the O31···O32 hydrogen bonds. This is the only remaining site for disorder, since the remaining coordination sites in each water molecule are already involved in hydrogen-bonds with an occupancy of 1.0 (for O31: O3-H···O31 and O31-H···p;for O32: N1-H···O32 and O32-H···O1). The coordinates of the O-Hand N-Hh ydrogen atoms were refined with restraints: DiscussionDuring the past few years al arge series of substituted phenylboronic acid derivatives have been prepared, mainly for applications in organic synthesis [1,2] and for molecular recognition of biochemically active molecules [3]. More recently, such boronic acid derivatives have attracted attention also as building blocks for the self-assembly of macrocyclic and polymeric assemblies. For this purpose, the boronic acid is generally converted to an ester (boronate) via condensation with an aliphatic or aromatic diol, which is then assembled to amacromolecular structure via reaction of the additional functional group attached to the B-phenyl ring [4][5][6]. In this context, 3-aminophenylboronic acid has been employed for the generation of macrocycles and cages [7][8][9][10][11]. In contrast to the analogous ester derived from pinacol [12], in this case the water adduct has been obtained, which has converted to the corresponding zwitterion and crystallized as dihydrate. A search of the Cambridge Structural Database (CSD, version 5.31) [13], revealed that there is no entry so far for an aqua complex of a boronic acid ester. Until now, solid-state structures of aqua-boron complexes have been reported only for triphenylborane derivatives, in particular for tris(pentafluorophenyl)borane [14,15]. The asymmetric unit of the aqua-catecholboronate contains one aqua-boronate and two uncoordinated water molecules (figure, top). Upon coordination to the boron atom the coordinated water molecule is deprotonated to form the corresponding zwitterion.

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Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages

Abstract: Simple one‐pot reactions: Boronate ester condensation reactions can be combined with imine condensations and metal–ligand interactions to build nanometer‐sized macrocycles and cages in one step from small building blocks (see scheme).

Cited by 224 publications

References 58 publications

Topological landscapes of porous organic cages

Topological landscapes of porous organic cages

Neutral discrete metal–organic cyclic architectures: Opportunities for structural features and properties in confined spaces

Crystal structure of aqua-2-(3-aminophenyl)-1,3,2-dioxaborole dihydrate, C12H12BNO3 · 2H2O

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