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Literature Meeting March 25, 2008 Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications David Marcoux Charette’s Laboratories
2 Importance (Natural Products)
3 Importance (Drugs)
5 Importance (Materials)
6 Common C(aryl)-N Bond Formation (Reductive Amination and Alkylation)
7 Common C(aryl)-N Bond Formation (S N Ar)
8 Common C(aryl)-N Bond Formation (Nitration)
9 Common C(aryl)-N Bond Formation (Ullman Reaction)
10 Common C(aryl)-N Bond Formation(Larock Indole Synthesis)
11 Common C(aryl)-N Bond Formation (Aryne Chemistry)
12 Common C(aryl)-N Bond Formation (Pd-Mediated)
13 Hartwig-Buchwald Pd-Catalyzed C(Aryl)-X Coupling
14 Pd-Catalyzed C-C Coupling
15 Catalytic Cycle
16 Generation of the Active Catalyst
17 Oxidative Addition
20 Reductive Elimination
21 -H Elimination
22 Migita First Results in Pd-Catalyzed C(Aryl)-N Bond Formation
23 Prof. John F. Hartwig
24 Hartwig First Look
25 Hartwig First Look
26 Catalytic Cycle with Tin Amide
27 Prof. Stephen L. Buchwald
28 Buchwald First Look
29 First Coupling Using Free Amine
30 First Coupling Using Free Amine
31 Intramolecular Version
32 Side Product
33 Real Problem
34 2 Weeks Later
35 Hartwig’s Conditions
36 Unsolved Problems
37 BINAP Scope
40 Why ArI are Less Reactive
41 Etheral Solvents
42 Lower Temperature
43 Why 18-C-6 ?
44 Pyridine Containing Substrates
45 Chiral Amine
46 Bidentate Ligand
50 Ligand Screening
53 From ArylOTf
54 Functionnal Groups Tolerance
55 Lower Temperature
56 Lower Temperature and ArCl
57 Lower Temperature and ArCl
59 Functionalized Arylclorides
60 Enlarging the Scope
61 C-H Functionalization
62 But Why NH 3 Can’t Be Used ?
63 Specific Case: Ammonia
64 Specific Case: Ammonia
65 Specific Case: Ammonia
66 Specific Case: Ammonia
67 Specific Case: Ammonia
68 Specific Case: Ammonia
69 First Coupling with NH 3(g)
70 More Convenient NH 3 Source
71 Reductive Elimination
72 With Ammonia
74 Sequential Addition
75 Total Synthesis
76 Total Synthesis
77 Total Synthesis
78 Synthesis of Analogs
79 Aryl Piperazine (large scale)
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