Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• been shown to be active in a variety of reduction/hydrogenation transformations employing dihydrogen as terminal reducing agent. Keywords: ball mill; bifunctional catalysis; catalytic hydrogenations; copper; mechanochemical synthesis; N-heterocyclic carbenes; Introduction Prominent goals of green

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

• Viera Poláčková,
• Dominika Krištofíková,
• Boglárka Némethová,
• Renata Górová,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

• aldehydes and hydrogen-bond activation of nitroalkenes. Keywords: asymmetric organocatalysis; hydrogen bond; Michael addition; pyrrolidine; thiourea; urea; Introduction Asymmetric organocatalysis became one of the strategic ways for the efficient synthesis of chiral compounds [1]. Bifunctional catalysis

The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

• Deniz Tözendemir and
• Cihangir Tanyeli

Beilstein J. Org. Chem. 2021, 17, 494–503, doi:10.3762/bjoc.17.43

• %) catalyst loading. Selected enantiomerically enriched sulfa-Michael addition products were subjected to oxidation to obtain the corresponding sulfones. Keywords: asymmetric synthesis; bifunctional catalysis; cinchona alkaloids; organocatalysis; sulfa-Michael reaction; Introduction Derivatives of the

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• , if both the nucleophile and the electrophile are activated independently by distinct functional groups on the same catalyst, this is referred to as bifunctional catalysis (Figure 2, (1)) [48]. When the two catalysts work in a cooperative way to activate only one substrate, this is classified as

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

• Anna Kmieciak and
• Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

• ], conjugated additions to enones [7], and allylic alkylations [8][9]. Another direction of research is the use of phosphines in organocatalysis [10][11] and bifunctional catalysis [12]. Several methods were developed to introduce the phosphine functionality to organic molecules. The reaction of organometallics

Green chemistry

• Luigi Vaccaro

Beilstein J. Org. Chem. 2016, 12, 2763–2765, doi:10.3762/bjoc.12.273

• , including “Strategies in asymmetric catalysis” by Tehshik P. Yoon [6], “Organometallic chemistry” by Bernd F. Straub and Lutz H. Gade [7], “C–H functionalization/activation in organic synthesis” by Richmond Sarpong [8], “Bifunctional catalysis” by Darren J. Dixon [9], “Sustainable catalysis” by Nicholas J

Bifunctional catalysis

• Darren J. Dixon

Beilstein J. Org. Chem. 2016, 12, 1079–1080, doi:10.3762/bjoc.12.102

• Darren J. Dixon Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK, Tel: +44 (0)1865 275648; Fax: +44 (0)1865 285002 10.3762/bjoc.12.102 Keywords: bifunctional catalysis; Bifunctional catalysis concerns the use of low molecular weight, structurally defined

• field continues to expand at an impressive pace. The present Thematic Series serves to highlight the current state-of-the-art of bifunctional catalysis from new bifunctional catalyst design and development, their application in new asymmetric metholodgy development, to their application in natural

Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction

• Qing He,
• Gu Zhan,
• Wei Du and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2016, 12, 309–313, doi:10.3762/bjoc.12.33

• allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized. Keywords: 7-azaisatins; β-isocupreidine; bifunctional catalysis; maleimide; MBH

A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates

• Hong-Bo Zhang,
• Yong-Chun Luo,
• Xiu-Qin Hu,
• Yong-Min Liang and
• Peng-Fei Xu

Beilstein J. Org. Chem. 2016, 12, 253–259, doi:10.3762/bjoc.12.27

• one-pot cascade quadruple protocol features readily available starting materials, simple manipulation, mild conditions and good atom economy. Keywords: bifunctional catalysis; hexahydroisoindolinones; one-pot synthesis; quadruple cascade; Introduction Isoindolines and their congeners are one kind of

• [65]. However, substrates with aliphatic R1, R2 or R3 did not produce the desired products (Table 2, entries 21–26). This bifunctional catalysis cascade reaction was also amenable to scale-up. When the reaction was carried out on a 3 mmol scale, the desired product was obtained in 84% yield. Therefore

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• atom. Although most of the studies on NHCs together with metal moieties are based on the interaction of the carbene carbon of the NHC with the metal [23][24][25][26], the high instability due the NH group of the pNHCs can induce secondary interactions leading to bifunctional catalysis [27][28

Catalytic asymmetric formal synthesis of beraprost

• Yusuke Kobayashi,
• Ryuta Kuramoto and
• Yoshiji Takemoto

Beilstein J. Org. Chem. 2015, 11, 2654–2660, doi:10.3762/bjoc.11.285

• the tricyclic core were controlled via Rh-catalyzed stereoselective C–H insertion and the subsequent reduction from the convex face. Keywords: bifunctional catalysis; hydrogen bonding; organocatalyst; oxa-Michael; prostacyclin; Introduction Prostacyclin (PGI2, Figure 1) is a physiologically active

Metal-mediated aminocatalysis provides mild conditions: Enantioselective Michael addition mediated by primary amino catalysts and alkali-metal ions

• Matthias Leven,
• Jörg M. Neudörfl and
• Bernd Goldfuss

Beilstein J. Org. Chem. 2013, 9, 155–165, doi:10.3762/bjoc.9.18

• ][13]. In most cases, transition or rare-earth metals are employed as Lewis acids in order to activate electrophilic compounds to react with substrates that are directly bonded to an organic catalyst [9][10][11][12][13]. An example is the enamine–metal Lewis acid bifunctional catalysis for asymmetric