Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

• Yafei Guo and
• Syuzanna R. Harutyunyan

Beilstein J. Org. Chem. 2020, 16, 1006–1021, doi:10.3762/bjoc.16.90

• asymmetric additions to N-heteroaromatic alkenyl compounds are less developed. This deficiency is largely due to the intrinsically low reactivity of alkenyl-substituted heterocycles towards nucleophilic addition compared to common Michael acceptors. A way to lift this barrier was introduced in 2016 by

• Harutyunyan and co-workers, who developed a general methodology for the direct and facile access to a variety of chiral heterocyclic aromatic compounds by the ACA of Grignard reagents to conjugated N-heteroaromatic alkenyl compounds (Scheme 14) [44]. The key of the presented method was the enhancement of the

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

• Hong Yan,
• Zhong-Yi Mao,
• Zhong-Wei Hou,
• Jinshuai Song and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76

• ] have studied the reactions of electrochemically generated NCRs. Particularly, we have recently reported an electrochemical synthesis of imidazo-fused N-heteroaromatic compounds via a radical cyclization cascade [31]. Building on this work, we report herein an atroposelective synthesis of

An efficient Pd–NHC catalyst system in situ generated from Na₂PdCl₄ and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

• Nan Sun,
• Meng Chen,
• Liqun Jin,
• Wei Zhao,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

• - and meta-substituted analogues (entries 16–18, Table 2). Besides the substituted phenyl bromides, 2-bromonaphthalene (1s) and some N-heteroaromatic bromides (3-bromopyridine (1t) and 3-bromoquinoline (1u)) could smoothly couple with 2a to afford the corresponding coupling products 3sa, 3ta and 3ua in

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• transformation of N-heteroaromatic salts into the corresponding N-ylides with epoxides was reported recently [5][17][18]. The next step represents a 1,3-dipolar cycloaddition of the bis(1,3-dipoles) 10 with formation of dihydro-indolizines 11 which, under the reaction conditions, are dehydrogenated to the final

Beyond catalyst deactivation: cross-metathesis involving olefins containing N-heteroaromatics

• Kevin Lafaye,
• Cyril Bosset,
• Lionel Nicolas,
• Amandine Guérinot and
• Janine Cossy

Beilstein J. Org. Chem. 2015, 11, 2223–2241, doi:10.3762/bjoc.11.241

• delineate some guidelines for the use of these challenging substrates in metathesis reactions. Keywords: catalyst deactivation; cross-metathesis; N-heteroaromatic; pyridine; ring-closing metathesis; Introduction Over the past decades, metathesis has become a key reaction within the organic chemist’s

• including alcohols, halides, esters, amides, carbamates and sulfonamides are compatible with the metathesis conditions [14][15][16][17][18][19][20]. However, the involvement of alkenes containing a nitrogen atom such as an amine or an N-heteroaromatic ring in metathesis reactions is still problematic and

• , a deprotonation of the metallacyclobutane is hypothesized to explain the amine-induced decomposition (Table 3). Consequently, a modulation of the Brønsted basicity and/or the nucleophilicity of the amine/N-heteroaromatic present on an alkene may allow its use in metathesis reactions. Ring-closing