Amines: Synthesis, Properties and Applications, 2004. ,
c) Amino Group Chemistry: From Synthesis to the Life Science, vol.1, 2007. ,
A General Approach to Catalytic Alkene Anti-Markovnikov Hydrofunctionalization Reactions via Acridinium Photoredox Catalysis, Angew. Chem. Int. Ed, vol.81, issue.2, pp.10075-10166, 1997. ,
, For reviews on hydroarylation of unactivated alkenes, see
A Review of New Developments in the Friedel-Crafts Alkylation, Beilstein J. Org. Chem, vol.6, 2010. ,
Transition Metal Catalyzed Hydroarylation of Olefins Using Unactivated Substrates: Recent Developments and Challenges, J. Organomet ,
) Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, Chem. Rev, vol.696, pp.9333-9403, 2011. ,
Uchimaru, Y. N?H Activation vs. C?H Activation: Ruthenium-Catalysed Regioselective Hydroamination of Alkynes and Hydroarylation of an Alkene with N-Methylaniline, Neuere Methoden der Präparativen Organischen Chemie II. 7. Alkyliering Aromatischer Amine. Angew. Chem, vol.22, issue.5, pp.6775-6779, 1957. ,
A simple Catalyst for the Efficient Benzylation of Arenes by Using Alcohols, Ethers, Styrenes, Aldehydes, or Ketones, Triflate-Catalyzed Intermolecular Hydroamination of Vinylarenes and Anilines: Scopes and Limitations, vol.15, pp.13594-13597, 2007. ,
Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides, Angew. Chem. Int. Ed, vol.51, pp.6486-6492, 2015. ,
, Org. Lett, vol.20, pp.3101-3104, 2018.
Branch-Selective and Enantioselective Iridium-Catalyzed Alkene Hydroarylation via Anilide-Directed C?H Oxidative Addition, J. Am. Chem. Soc, vol.20, pp.9055-9059, 2018. ,
Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols, For a related example involving benzylic alcohols instead of styrenes, vol.9, pp.14193-14195, 2006. ,
Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis, Angew. Chem. Int. Ed, vol.55, pp.14245-14249, 2016. ,
Chemoselective Borane-Catalyzed Hydroarylation of 1,3-Dienes with Phenols, Angew. Chem. Int. Ed, vol.141, pp.1694-1699, 2019. ,
Recent Advances in Metal-Free and Late Transition Metal-Catalysed Hydroamination of Unactivated Alkenes, Organic Reactions, vol.42, pp.2596-2697, 2003. ,
A Highly Active Palladium Catalyst for Intermolecular Hydroamination. Factors that Control Reactivity and Additions of Functionalized Anilines to Dienes and Vinylarenes, Angew. Chem. Int. Ed, vol.88, issue.11, pp.1774-1777, 2000. ,
Visible-Light-Induced Copper-Catalyzed Intermolecular Markovnikov Hydroamination of Alkenes, Org. Lett, vol.21, pp.7873-7877, 2019. ,
Calcium(II)-and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol, Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synlett, vol.5, pp.7405-7409, 2004. ,
Booster Effect" of Fluorinated Alcohol Solvents: Aggregation-Induced Conformational Changes and Cooperatively Enhanced H-Bonding, J. Am. Chem. Soc, vol.128, pp.13412-13420, 2006. ,
Overcoming Product Inhibition in Catalysis of the Intramolecular Schmidt Reaction, J. Am. Chem. Soc, vol.135, pp.9000-9009, 2013. ,
Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to ?-or ?-Lactams, Angew. Chem. Int. Ed, vol.138, pp.8528-8533, 2016. ,
HFIP Solvent Enables Alcohols to Act as Alkylating Agents in Stereoselective Heterocyclization, Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17, vol.10, pp.6489-6493, 2018. ,
Synthesis of Bridged Tetrahydrobenzo[b]azepines and Derivatives through an Aza-Piancatelli cyclization/Michael Addition Sequence, Angew. Chem. Int. Ed, vol.21, pp.1134-1138, 2019. ,
During the preparation of this manuscript, Colomer reported the hydroarylation of electron-rich alkenes with anilines. The overall transformation and key to reactivity (HFIP) are the same, J. Polym. Res, vol.20, issue.17, pp.128-133, 2013. ,
Carbon-Carbon and Carbon-Heteroatom Bond-Forming Transformations Catalyzed by Calcium(II) Triflimide, Besides, we tested his catalytic system (NaOAc in HFIP) in our model reaction between 1a and 2a and we did not observe any reactivity, vol.10, pp.15171-15174, 2011. ,
Although diphenylamine 2a was used in excess (4 equivalents), it could be easily recovered by flash column chromatography during the purification of the crude material. (21) The reaction was also attempted with activated alkenes such as ethyl acrylate but led only to the aza-Michael addition product. (22) For those pKa values, see: Kaljurand, J. Phys. Org. Chem, vol.22, issue.20, pp.171-181, 2013. ,
In our attempts to determine the reactive species, we performed NMR studies, which suggests the formation of Ca(NTf 2 )(OCH(CF 3 ) 2 ) when mixing Ca, J. Chem. Soc, vol.117, issue.25, pp.103-137, 1920. ,
Potassium and Well-Defined Neutral and Cationic Calcium Fluoroalkoxide Complexes: Structural Features and Reactivity, For the stabilization of calcium salts via Ca···F interactions, vol.133, pp.2482-2505, 2011. ,
URL : https://hal.archives-ouvertes.fr/hal-01114341
Synthesis and Stabilization-Advances in Organoalkaline Earth Metal Chemistry, Chem. Commun, vol.46, issue.27, pp.4449-4465, 2010. ,
Coordination of Arenes and Phosphines by Charge Separated Alkaline Earth Cations, Organometallics, vol.35, pp.12684-12693, 2016. ,
Krossing, I. Soft Interactions with Hard Lewis Acids: Generation of Mono-and Dicationic Alkaline-Earth Metal Arene-Complexes by Direct Oxidation, Organometallics, vol.38, pp.2068-2076, 2019. ,
Intermolecular Pd(II)-Catalyzed Oxidative Biaryl Synthesis Under Air: Reaction Development and Scope, J. Org. Chem, vol.73, pp.5022-5028, 2008. ,
Efficient Dehydrogenation of 1,2,3,4-Tetrahydroquinolines Mediated by Dialkyl Azodicarboxylates, Synth. Commun, vol.48, pp.1291-1298, 2018. ,
Catalytic Electrophilic Alkylation of p-Quinones through a Redox Chain Reaction, Angew. Chem. Int. Ed, vol.56, pp.8196-8200, 2017. ,
Reduction with Metal Borohydride-Transition Metal Salt System. I. Reduction of Aromatic Nitro Compounds with Potassium Borohydride-Copper(I) Chloride, Synth. Commun, vol.19, pp.3047-3050, 1989. ,