Friedel-Crafts Alkylation

This Lewis Acid-catalyzed Electrophilic Aromatic Substitution Allows The Synthesis Of Alkylated Products Via The Reaction Of Arenes With Alkyl Halides Or Alkenes. Since Alkyl Substituents Activate The Arene Substrate, Polyalkylation May Occur. A Valuable, Two-step Alternative Is Friedel-Crafts Acylation Followed By A Carbonyl Reduction.

---

Mechanism Of The Friedel-Crafts Alkylation

Using Alkenes :

Recent Literature

Iron Oxide Nanoparticles Grown On Carboxy-Functionalized Graphite: An Efficient Reusable Catalyst For Alkylation Of Arenes
V. Rajpara, S. Banerjee, G. Sereda, Synthesis, 2010, 2835-2840.

Dicationic Electrophiles From Olefinic Amines In Superacid
Y. Zhang, A. McElrea, G. V. Sanchez, D. Do, A. Gomez, S. L . Aguirre, R. Rendy, D. A. Klumpp, J. Org. Chem., 2003, 68, 5119-5122.

Benzylic Phosphates In Friedel-Crafts Reactions With Activated And Unactivated Arenes: Access To Polyarylated Alkanes
G. Pallikonda, M. Chakravarty, J. Org. Chem., 2016, 81, 2135-2142.

Samarium Triflate-Catalyzed Halogen-Promoted Friedel-Crafts Alkylation With Alkenes
S. Haira, B. Maji, S. Bar, Org. Lett., 2007, 9, 2783-2786.

Dramatic Enhancement Of Catalytic Activity In An Ionic Liquid: Highly Practical Friedel-Crafts Alkenylation Of Arenes With Alkynes Catalyzed By Metal Triflates
C. E. Song, D.-U. Jung, S. Y. Choung, E. J. Roh, S.-G. Lee, Angew. Chem. Int. Ed., 2004, 43, 6183-6185.

MA-Silica Gel Catalyzed Propargylation Of Aromatic Compounds With Arylpropargyl Alcohols Under Solvent-Free Conditions
P. Srihari, J. S. S. Reddy, S. S. Mandal, K. Satyanarayana, J. S. Yadav, Synthesis, 2008, 1853-1860.

Unexpected Formation Of 3-Substituted 1,2,3,4-Tetrahydroisoquinolines During Tosylation Of N,N-dibenzylaminols
S. Chandrasekhar, P. K. Mohanty, K. Harikishan, P. K. Sasmal, Org. Lett., 1999, 1, 877-879.

Iron-Catalyzed Synthesis Of Tetrahydronaphthalenes Via 3,4-Dihydro-2H-pyran Intermediates
R. B. Watson, C. S. Schindler Org. Lett., 2018, 20, 68-71.

Metal-Free Tandem Friedel–Crafts/Lactonization Reaction To Benzofuranones Bearing A Quaternary Center At C3 Position
L. Chen, F. Zhou, T.-D. Shi, J. Zhou, J. Org. Chem., 2012, 77, 4354-4362.

Addition Of Arylboronic Acids To Arylpropargyl Alcohols En Route To Indenes And Quinolines
J. Panteleev, R. Y. Huang, E. K. J. Lui, M. Lautens, Org. Lett., 2011, 13, 5314-5317.

Conversion Of 2-Alkylcinnamaldehydes To 2-Alkylindanones Via A Catalytic Intramolecular Friedel-Crafts Reaction
G. B. Womack, J. G. Angeles, V. E. Fanelli, C. A. Heyer, J. Org. Chem., 2007, 72, 7046-7049.