Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

• Austin Pounder,
• Eric Neufeld,
• Peter Myler and
• William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• 2012, Singh and co-workers performed green syntheses of oxa-aza-benzo[a]anthracene and oxa-aza-phenanthrene derivatives 151 and 152 via a sequential one-pot reaction in an aqueous micellar system (Scheme 34) [68]. This methodology comprised reactions of isoquinoline (147), phenacyl bromides 148 bearing

• -phenanthrene derivatives 152, also in excellent yields (91–98%) [68]. In 2015, Gribble et al. published a new method to synthesize dibenzo[a,c]anthracene (158) based on a triple benzannulation of naphthalene derivative 153 via a 1,3,6-naphthotriyne synthetic equivalent 155 (Scheme 35) [69]. First, reaction of

• metathesis strategy to synthesize benz[a]anthracenes. Green synthesis of oxa-aza-benzo[a]anthracene and oxa-aza-phenanthrene derivatives. Triple benzannulation of substituted naphtalene via a 1,3,6-naphthotriyne synthetic equivalent. Zinc iodide-catalyzed Diels–Alder reactions with 1,3-dienes and aroyl

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

• Alessandra Del Tito,
• Havall Othman Abdulla,
• Davide Ravelli,
• Stefano Protti and
• Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

• -bromochalcones (Scheme 3). Thus, compounds 3.1a–d underwent a one-electron reduction by the excited photocatalyst fac-Ir(ppy)3. Upon bromide anion loss, the α-keto vinyl radicals 3.2·a–d were then formed, which smoothly added onto the vicinal aromatic ring in an intramolecular fashion, affording phenanthrene

• derivatives 3.3a–d upon rearomatization. Notably, the process offers a wide substrate scope and the products are obtained with complete regioselectivity [43]. 2 Synthesis of phenanthridines or related azaarenes Under photocatalyzed conditions, phenanthridines are mostly obtained via an intramolecular radical

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

• Yue Zhong,
• Wen-Yu Wu,
• Shao-Peng Yu,
• Tian-Yuan Fan,
• Hai-Tao Yu,
• Nian-Guang Li,
• Zhi-Hao Shi,
• Yu-Ping Tang and
• Jin-Ao Duan

Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26

• palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C–H activation, decarbonylation and subsequent a retro-Diels–Alder process. Pleasantly, this protocol has a wider

• substrate range, shorter reaction times and higher yields of products than previously reported methods. Keywords: C–H activation; norbornadiene; palladium; phenanthrene derivatives; Introduction Phenanthrene is a polycyclic aromatic hydrocarbon which contains three benzene rings. The phenanthrenes can be

• ], antibacterial [6], anti-inflammatory [7] and so on. During the past decades, numerous methods for the preparation of phenanthrene derivatives have been developed. In 2003, Gabriel Tojo’s group reported a base-catalyzed photochemical synthesis of phenanthrene derivatives [8] through intramolecular aromatic

Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

• Quentin Lefebvre,
• Marc Jentsch and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 1883–1890, doi:10.3762/bjoc.9.221

• photocyclization of tri- and tetrasubstituted olefins were reported [16][25]. Therefore, we decided to demonstrate our methodology on both di- and trisubstituted olefins (Table 3). We disclose here the first photocyclization of trisubstituted olefins in flow, giving access to backbone-functionalised phenanthrene

• derivatives. We choose stilbenes with bromide and methyl substituents, as the latter can be used in subsequent oxidation, deprotonation, and radical addition reactions, whereas the former opens access to various functional groups via lithium-halogen exchange or cross-coupling chemistry. Methoxy groups were

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• Friedel–Crafts/furan–yne cyclization/heteroenyne metathesis was developed for the highly efficient construction of phenanthrene derivatives 270 [144]. Both AuCl3 and PPh3AuCl are effective catalysts for all the processes in the reaction and a variety of diyne substrates 271 could be used (Scheme 48