Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
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1 Catellani Reaction (Pd-Catalyzed Sequential Reaction) Todd Luo
2 Content Introduction Progress of Catellani Reaction o-alkylation and Applications o-arylation and Applications Conclusion and Outlook 2
3 Introduction Typical Catellani Reaction Main characters of Catellani Reaction Versatile method for C-C coupling Selective ortho C-H functionalization Co-catalytic system (Pd and norbornene) 3
4 4 General Mechanism
5 o-alkylation Challenges: How to control selective oxidative addition of Pd 0 with iodobenzene? How to control selective oxidative addition of Pd II (13) with alkyl iodide? How to control selective reaction of TA with Pd II (14)? Solutions: At room temperature: To Pd 0 : Aryl-X > Alkyl-X To Pd II : Aryl-X < Alkyl-X Increase the use of Norbornene and Alkyl-X Choose a suitable Terminating Agent (TA) Good terminating events Mizoroki-Heck Coupling, Suzuki-Miyaura Coupling, Cassar-Sonogashira Coupling, 5 Cyanation, Direct Arylation, Amination, Hydrogenolysis, etc.
6 o-alkylation and Application The first example of Catellani Reaction Proposed a suitable reaction mechanism Terminating event is Mizoroki-Heck Coupling 6 Catellani, M. etc. Angew. Chem. Int. Ed. Engl. 1997, 36, 119.
7 o-alkylation and Application Terminating event is Suzuki- Miyaura Coupling. Efficient way to synthesize 2,6-disubstituted biphenyls. 2,6-disubstituted biphenyls can be used as ligand. 7 Catellani, M. etc. J. Chem. Soc. Chem. Commun. 2000, 157.
8 o-alkylation and Application Terminating event is Cassar- Sonogashira Coupling Diphenylacetylene is not suitable for the reaction. 8 Catellani, M. etc. J. Organomet. Chem. 2004, 689, 3741.
9 o-alkylation and Application The first time to synthesize o,o -differently substituted vinylarenes. Problems Using different alkyl iodides leads to all the possible combinations of the ortho substituents. Using pre-substituted aryl iodide leads to competed elimination byproduct. Solutions Increasing the use of Alkyl iodide. Adding KOAc could lead good result. 9 Catellani, M. etc. Tetrahedron 1999, 55, 6595.
10 o-alkylation and Application Achievements Using TFP as ligand can efficiently promote o-alkylation. Applying Catellani Reaction to synthesize condensed ring. 10 Lautens, M. etc. Angew. Chem. Int. Ed. Engl. 2000, 39, 1045; J. Org. Chem. 2001, 66, 8127.
11 o-alkylation and Application Achievements Combining the Catellani Reaction with an aza-michael addition reaction to synthesize condensed rings. 11 Catellani, M. etc. Tetrahedron Lett. 2004, 45, 6903.
12 o-alkylation and Application Achievements First example of using alkyl chloride as alkylation source. 12 Ferraccioli, R. etc. Eur. J. Org. Chem. 2009, 3161.
13 o-alkylation and Application Achievements Exploring ways of synthesizing polycycles. 13 Lautens, M. etc. Org. Lett. 2003, 5, 4827; J. Org. Chem. 2007, 72, 775.
14 o-alkylation and Application Achievements Expanding the Catellani Reaction to hereroaryl iodides. 14 Lautens, M. etc. Org. Lett. 2006, 8, 3939.
15 o-alkylation and Application Achievements The first example of terminating Catellani reaction with Cyanation. -CN can be transformed into -COOH, -CONH 2, -CH 2 NH 2, etc. 15 Lautens, M. etc. J. Am. Chem. Soc. 2006, 128,
16 o-alkylation and Application Achievement Examples of terminating Catellani reaction with Direct Arylation. 16 Lautens, M. etc. J. Am. Chem. Soc. 2005, 127, 13148; Org. Lett. 2006, 8, 2043; Org. Lett. 2006, 8, 3601; Org. Lett. 2006, 8, 4827; J. Org. Chem. 2008, 73, J. Org. Chem. 2008, 73, 8705; J. Org. Chem. 2008, 73, 9164.
17 o-alkylation and Application Helical Alkenes are widely used in material science. 17 Lautens, M. etc. Tetrahedron 2008, 64, 6002; Angew. Chem. Int. Ed. Engl. 2012, 51, 9846.
18 o-alkylation and Application Achievements The first example of terminating Catellani reaction with Amination. Creating another way of synthesizing condensed hetero-rings. 18 Lautens, M. etc. Org. Lett. 2007, 9, 5255.
19 o-alkylation and Application H-donor: alkyl halide, alkylboronic acid, benzyl alcohol. Achievement Terminating event is Hydrogenolysis. 19 Lautens, M. etc. Org. Lett. 2005, 7, 4053; Org. Lett. 2008, 10, 5095.
20 The beginning of o-arylation In the absence of norbornene In the presence of norbornene 20 Catellani, M. etc. J. Organomet. Chem. 1985, 286, C13; J. Organomet. Chem. 1998, 584, 63.
21 o-arylation and Application Achievement Terminating event is Heck Coupling. 21 Catellani, M. etc. Synthesis. 2003, 2671.
22 o-arylation and Application Achievement The first time to introduce an alkyl chain containing carbonyl group. 22 Catellani, M. etc. J. Organomet. Chem. 2003, 687, 473.
23 o-arylation and Application 23 Incorporation of diphenylacetylene, formation of condensed arenes. Catellani, M. etc. Org. Lett. 2001, 3, 3611.
24 o-arylation and Application Achievement Terminating event is Suzuki Coupling. 24 Catellani, M. etc. J. Mol. Catal. A: Chem. 2003, , 115.
25 o-arylation and Application 25 Terminating event is Hydrogenolysis. Catellani, M. etc. Can. J. Chem. 2005, 83, 741.
26 o-arylation and Application To Pd 0 : Aryl-I > Aryl-Br To Pd II : Aryl-I < Aryl-Br Big Progress 26 Coupling with two different aryl halide (Cross Coupling).
27 o-arylation and Application Achievement The first example of Cross Coupling. Terminating event is Heck Coupling. 27 Catellani, M. etc. J. Am. Chem. Soc. 2004, 126, 78.
28 o-arylation and Application 28 Catellani, M. etc. J. Am. Chem. Soc. 2004, 126, 78.
29 o-arylation and Application 29 Mechanism of Cross Coupling
30 o-arylation and Application Terminating event is Cyanation. 30 Lautens, M. etc. J. Am. Chem. Soc. 2007, 129,
31 o-arylation and Application Achievements Combining Catellani Reaction with Michael-Type Addition. Efficient way to synthesize condensed hetero-ring. 31 Catellani, M. etc. Org. Lett. 2006, 8, 3967.
32 o-arylation and Application Achievements 32 Combining Catellani Reaction with aza-michael Addition. Catellani, M. etc. Adv. Synth. Catal. 2008, 350, 2513; Adv. Synth. Catal. 2010, 352, 1451.
33 o-arylation and Application Achievements Terminating Catellani Reaction with C-N Coupling. Exploring way of synthesizing hetero-aromatic ring. 33 Catellani, M. etc. Adv. Synth. Catal. 2008, 350, 2179.
34 o-arylation and Application Achievements Expanding reaction to heteroaryl bromide. 34 Catellani, M. etc. Org. Lett. 2004, 6, 4759.
35 o-arylation and Application These polycyclic condensed heteroaryl rings are good candidates for pharmaceutics. 35 Catellani, M. etc. J. Am. Chem. Soc. 2006, 128, 722.
36 o-arylation and Application Using imine as reagent to directly synthesize polycyclic condensed heteroaryl rings. 36 Lautens, M. etc. Angew. Chem. Int. Ed. Engl. 2009, 48, 6713.
37 o-arylation and Application Strategy A new way of synthesizing polycyclic condensed heteroaryl rings. 37 Malacria, M. etc. Org. Lett. 2010, 12, 5692.
38 o-arylation and Application Putting the amine group at a proper position can lead to form a new cycle. 38 Lautens, M. etc. J. Org. Chem. 2010, 75, 3495.
39 o-arylation and Application 90: Nucleophile 90: Electrophile Switching the reactivity of Pd II by changing the reaction condition. 39 Lautens, M. etc. Angew. Chem. Int. Ed. Engl. 2009, 48, 1849.
40 Summary and Outlook Summary Outlook Exploring ways of ortho C-H funtionalization. Exploring ways of initial step. 40 Recent Achievement: J. Am. Chem. Soc. 2011, 133, 12990; J. Am. Chem. Soc. 2012, 134, 14563; J. Am. Chem. Soc. 2013, 135, 9318; Angew. Chem. Int. Ed. Engl. 2013, 52, 6080; J. Am. Chem. Soc. 2013, DOI:ja410823e. Important Reviews: Synthesis 2013, 45, 581; Top. Curr. Chem. 2010, 292, 1. Acc. Chem. Res. 2008, 41, Top. Organomet. Chem. 2005, 14, 21.
41 41
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