Copper-catalyzed monoselective C–H amination of ferrocenes with alkylamines

• Zhen-Sheng Jia,
• Qiang Yue,
• Ya Li,
• Xue-Tao Xu,
• Kun Zhang and
• Bing-Feng Shi

Beilstein J. Org. Chem. 2021, 17, 2488–2495, doi:10.3762/bjoc.17.165

• Fukuzawa and Kanemoto [50]. Notably, our method proceeded under silver-free conditions at relatively lower temperature and in shorter time, providing a complementary alternative to the work of Fukuzawa and Kanemoto. Results and Discussion We initiated our study by investigating the C–H amination of

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• one electron oxidations to form monomeric Pd(III) complexes have also been studied [251], but the successful implementation of silver-free conditions with stoichiometric palladium herein would appear to eliminate this as a key step. To the best of our knowledge, the existence of Pd(IV) complexes has

Simple activation by acid of latent Ru-NHC-based metathesis initiators bearing 8-quinolinolate co-ligands

• Julia Wappel,
• Roland C. Fischer,
• Luigi Cavallo,
• Christian Slugovc and
• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 154–165, doi:10.3762/bjoc.12.17

• -heterocyclic carbene bearing precursor complexes M31, HovII or M32 with excess of 5,7-dichloro-8-hydroxyquinoline or 5,7-dibromo-8-hydroxyquinoline in the presence of excess Cs2CO3 as the base (see Scheme 1). The silver-free method [41] resulted in any case in the formation of at least two new products (as

Influence of bulky yet flexible N-heterocyclic carbene ligands in gold catalysis

• Alba Collado,
• Scott R. Patrick,
• Danila Gasperini,
• Sebastien Meiries and
• Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 1809–1814, doi:10.3762/bjoc.11.196

• trifluoromethanesulfonimide. Following this silver-free procedure, [Au(ITent)(OH)] complexes 4–6 were reacted with HNTf2 to obtain the corresponding [Au(ITent)(NTf2)] species 7–9 which were isolated as white solids in good to excellent yields (Scheme 2). Complexes 7–9 were characterised by 1H, 13C{1H}, and 19F{1H} NMR

• measurements in solution of the [Ni(ITent)CO3] complexes [21][42]. Synthesis of gold complexes bearing the ITent ligands. Silver-free synthesis of [Au(ITent)(NTf2)] complexes. Influence of the ITent ligands in gold-catalysed alkyne hydration.a Influence of the ITent ligands in gold-catalysed nitrile

Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand

• Thibault E. Schmid,
• Florian Modicom,
• Adrien Dumas,
• Etienne Borré,
• Loic Toupet,
• Olivier Baslé and
• Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 1541–1546, doi:10.3762/bjoc.11.169

• Cedex, France 10.3762/bjoc.11.169 Abstract A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr)(picolinate)RuCl(indenylidene) complex 4a (SIPr = 1,3-bis(2-6

• in model ring closing metathesis and cross-metathesis transformations. Results and Discussion With the objective to develop an attractive strategy for the synthesis of indenylidene-picolinic ruthenium complexes, we initially attempted their preparation using a silver-free methodology. In fact, silver

New developments in gold-catalyzed manipulation of inactivated alkenes

• Michel Chiarucci and
• Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

• was heated in presence of the silver free gold complex 20c a variety of highly substituted azabicyclo[4.2.0]oct-5-enes 84 was obtained in good yields as a single regio- and diastereoisomer. The protocol displayed excellent functional group compatibility and efficient transfer of chirality was observed

Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes

• Marcia E. Richard,
• Daniel V. Fraccica,
• Kevin J. Garcia,
• Erica J. Miller,
• Rosa M. Ciccarelli,
• Erin C. Holahan,
• Victoria L. Resh,
• Aakash Shah,
• Peter M. Findeis and
• Robert A. Stockland Jr.

Beilstein J. Org. Chem. 2013, 9, 2002–2008, doi:10.3762/bjoc.9.235

• ; gold; gold catalysis; hydrophenoxylation; silver-free; single component; solvent-free; Introduction The use of gold compounds to promote hydroelementation reactions has grown tremendously over the past few years [1][2][3][4][5]. Using this approach, a host of different organic substrates have been

• the addition reaction [11]. Additionally, these cationic gold species can be generated through the reaction of chlorogold compounds with silver salts [1][2][3][4]. Recently, there has been growing interest in developing approaches that generate a catalytically active species under acid-free and silver

• -free conditions [12][13]. To this end, we have synthesized and investigated a series of arylgold compounds as single-component catalysts for hydroelementation reactions under acid, silver, and solvent-free conditions. We recently reported the synthesis of arylgold compounds using a focused microwave

Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

• Michel Chiarucci,
• Mirko Locritani,
• Gianpiero Cera and
• Marco Bandini

Beilstein J. Org. Chem. 2011, 7, 1198–1204, doi:10.3762/bjoc.7.139

• conditions (Table 1). Initial attempts to perform the lactonization reaction of 1a were carried out by means of a silver-free cationic complex [P(t-Bu)2o-biphenyl](AuCH3CN)SbF6 (5 mol %). The desired butyrolactone 2a was obtained selectively under reflux in DCE for 16 h (entry 1), although only in low yield

The role of silver additives in gold-mediated C–H functionalisation

• Scott R. Patrick,
• Ine I. F. Boogaerts,
• Sylvain Gaillard,
• Alexandra M. Z. Slawin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2011, 7, 892–896, doi:10.3762/bjoc.7.102

• (°) for 3: Au1–C1 1.978(5), Au1–O1 2.048(4), O1–C2 1.299(8), C2–O2 1.231(9), C1–Au1–O1 178.0(2), Au1–O1–C2 120.7(4), O1–C2–O2 124.6(6). Silver-free C–H functionalisation using [Au(OH)(IPr)]. C–H functionalisation of 2 using gold-phosphine complexes and a silver additive. Carboxylation of 2 using 1 and

Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF₂

• Lukas J. Gooßen,
• Bettina Zimmermann and
• Thomas Knauber

Beilstein J. Org. Chem. 2010, 6, No. 43, doi:10.3762/bjoc.6.43

• nitrobenzoic acids are successfully coupled with several olefins to give the corresponding vinyl arenes in moderate to good yields. Results and Discussion In our search for a silver-free catalyst system for decarboxylative Heck reactions, we chose the conversion of 2-nitrobenzoic acid (1a) with styrene (2a) to

• described by Forgione, Bilodeau and Liu [26][27] are limited to particularly activated, mostly 2,6-disubstituted or heterocyclic derivatives. We conclude from the fact that Myers’ protocol – in contrast to the silver-free version by Su – has a somewhat broader scope, that it allows for an additional