(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• compounds. 1,2-Disubstituted cubane The final ortho-benzene isostere which will be discussed is 1,2-disubstituted cubane (1,2-cubane) [14][51]. No complete set of exit vector parameters of 1,2-cubanes is available in literature but substituent distances and angles in 1,2-cubanes have been reported and show

• close similarity to the corresponding ortho-benzenes (Figure 15) [14][51]. Even though no value for the dihedral angle θ of disubstituted cubane has been reported, it is likely that the values of θ are approximately equivalent, given the forced coplanarity of the substituents in both cubane and benzene

• [52]. Routes to 1,4-cubanes have been available since the first syntheses of cubane derivatives by Eaton and co-workers [52][53]. Conversion of 1,4-cubanes to other disubstituted cubanes via a complex synthetic sequence has also been reported [54]. Recently, MacMillan and co-workers disclosed the

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• reactions. The “Co4O4” cubane complex Co4O4(CO2Me)4(RNC5H4)4 (R = CN, Br, H, Me, OMe), serves as a molecular catalyst for the efficient and stable photocatalytic water oxidation and CO2 reduction. A comprehensive structure–function analysis emerged herein, highlights the regulation of electronic

• characteristics for a molecular catalyst by selective ligand modification. This work demonstrates a modulation method for fabricating effective, stable and earth-abundant molecular catalysts, which might facilitate further innovation in the function-led design and synthesis of cubane clusters for photoredox

• reactions. Keywords: CO2 reduction; cobalt cubane; photocatalysis; water oxidation; water splitting; Introduction The direct conversion of solar energy into chemical fuels (e.g., H2, CO and hydrocarbons) through water splitting and carbon fixation reactions is a sustainable solution to environmental

Design and synthesis of novel bis-annulated caged polycycles via ring-closing metathesis: pushpakenediol

• Sambasivarao Kotha and
• Mirtunjay Kumar Dipak

Beilstein J. Org. Chem. 2014, 10, 2664–2670, doi:10.3762/bjoc.10.280

• the design and synthesis of natural as well as non-natural products [3][4]. Several intricate targets (Figure 1), such as snoutane (1) [18], basketane (2) [19], tetrahedrane (3) [20], triprismane [21], rocketene (4) [22], cubane (5) [23], garudane (6) [24], dodecahedrane (7) [25][26] and golcondane (8

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• for CuAAC reactions under Click conditions [144]. These copper(I) complexes can be handled under aerobic conditions and have been fully characterized including single crystal X-ray structures, which show a cubane-like [Cu4Br4] scaffold. Their main advantages are the ease of preparation, tolerance

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• attractive for a long time because they often lead to products that are otherwise virtually inaccessible by thermal reactions. The syntheses of highly strained molecules such as cubane [1] and pagodane [2] are famous examples. However, it is often difficult to predict and control the outcome of photochemical

A chemist and biologist talk to each other about caged neurotransmitters

• Graham C.R. Ellis-Davies

Beilstein J. Org. Chem. 2013, 9, 64–73, doi:10.3762/bjoc.9.8

• a series of important muscle physiology studies in the 1980s [6][10][11][12][13]. Chemists have been much more resistant to embrace the moniker, mostly because the term is used for cagelike structures (e.g., cubane), but also perhaps due to the “lateness of arrival” into the field, which gave rise

Flow photochemistry: Old light through new windows

• Jonathan P. Knowles,
• Luke D. Elliott and
• Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

• ; basic ketone photochemistry such as α- and β-cleavage; as well as fundamental concepts such as the singlet and triplet states and n,π* and π,π* excited states. From the late 1950s onwards thousands of examples of the application of photochemistry in synthesis were reported. Eaton's cubane synthesis [4

Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions

• Kyle F. Biegasiewicz,
• Michelle L. Ingalsbe,
• Jeffrey D. St. Denis,
• James L. Gleason,
• Junming Ho,
• Michelle L. Coote,
• G. Paul Savage and
• Ronny Priefer

Beilstein J. Org. Chem. 2012, 8, 1814–1818, doi:10.3762/bjoc.8.207

• , MA 01119, USA 10.3762/bjoc.8.207 Abstract Recently, a novel chiral cubane-based Schiff base ligand was reported to yield modest enantioselectivity in the Henry reaction. To further explore the utility of this ligand in other asymmetric organic transformations, we evaluated its stereoselectivity in

• above the copper center and limits the asymmetric control with this ligand. Keywords: chiral ligand; cubane; M06L and B3LYP calculations; Michael addition; Introduction Since the initial synthesis of cubane in 1964 by Eaton and Cole [1][2], numerous studies have been undertaken on its derivatives

• : Nitrated cubanes are remarkably explosive [3][4]; cubylamines possess antiviral activity [5]; and cubylamides have been shown to be P2X7 receptor antagonists [6]; whereas other cubane derivatives were examined as narcotic antagonists against both μ and ĸ receptors [7], as well as being monoamine oxidase

Reciprocal polyhedra and the Euler relationship: cage hydrocarbons, C_nH_n and closo-boranes [B_xH_x]²⁻

• Michael J. McGlinchey and
• Henning Hopf

Beilstein J. Org. Chem. 2011, 7, 222–233, doi:10.3762/bjoc.7.30

• closo-boranes BxHx+2, or their corresponding anions [BxHx]2− (where x = 5 through 12) and polycycloalkanes CnHn (where n represents even numbers from 6 through 20) exhibit a complementary relationship whereby the structures of the corresponding molecules, e.g., [B6H6]2− and C8H8 (cubane), are based on

• reciprocal polyhedra. The vertices in the closo-boranes correspond to faces in its polycyclic hydrocarbon counterpart and vice versa. The different bonding patterns in the two series are described. Several of these hydrocarbons (cubane, pentagonal dodecahedrane and the trigonal and pentagonal prismanes) are

• known while others still remain elusive. Synthetic routes to the currently known CnHn highly symmetrical polyhedral species are briefly summarized and potential routes to those currently unknown are discussed. Finally, the syntheses of the heavier element analogues of cubane and the prismanes are