Scheme 1
General catalytic cycles for the Pd-catalysed reactions.
Scheme 2
Sequential Suzuki reactions in the synthesis of D159687 (1).
Figure 1
PDE4D allosteric modulators D159404 (4) and D159153 (5).
Scheme 3
Suzuki reaction of an aryl chloride en route to 9.
Scheme 4
Optimized Suzuki reaction for the synthesis of 10.
Scheme 5
Suzuki reaction for the synthesis of PF-01367338 (14).
Scheme 6
Synthesis of 17 by means of a Suzuki reaction with the advanced boron pinacolate intermediate 19.
Scheme 7
Synthesis of boron pinacolate derivative 19.
Scheme 8
Synthesis of GDC-0941 (24) through a Suzuki reaction of THP-protected boronic acid 26.
Scheme 9
Optimized Suzuki reaction en route to 28.
Scheme 10
Suzuki-like reaction of acid chloride 33 for the synthesis of 32.
Scheme 11
First generation conditions or the Suzuki reaction aiming at 36.
Scheme 12
Optimized Suzuki reaction in the synthesis of 36.
Scheme 13
Aiming at 42 by means of a Suzuki reaction.
Scheme 14
Optimized synthesis of 42.
Figure 2
Examples of PI3K selective inhibitors.
Scheme 15
Suzuki reaction of iodothiophenes
Scheme 16
Retrosynthetic plan for the final steps of the Walker et al.36 large-scale synthesis of AMG 837 (53).
Scheme 17
Original Suzuki reaction employed for the synthesis of biphenyl 54.
Scheme 18
Optimized preparation of biphenyl 54.
Scheme 19
Simplified initial route for preparation of compounds 63.
Scheme 20
Modified Suzuki reaction in the synthesis of 62.
Scheme 21
Employment of a different solvent system for the Suzuki reaction en route to 62.
Scheme 22
Low loading of Pd in a Suzuki reaction for the synthesis of 66.
Scheme 23
A Suzuki reaction followed by ozonolysis for the preparation of 69.
Scheme 24
Preparation of 76 by means of a Suzuki reaction with activation of a sp3 carbon.
Scheme 25
Key steps in the synthesis of 77.
Figure 3
Chiral ligand employed for the asymmetric Suzuki reaction of 81.
Scheme 26
Synthesis of 84 with a Negishi coupling as key step.
Scheme 27
Synthesis of 88 with low loadings of Pd in a Negishi coupling.
Scheme 28
Optimal Sonogashira conditions for the synthesis of 92.
Scheme 29
Sonogashira cross-coupling with alkynyl pyridine 99.
Scheme 30
Heck reaction as a tool for assembling the isoquinoline ring of 101.
Scheme 31
Sonogashira reaction between bromide 110 and advanced alkyne 109.
Scheme 32
Intramolecular Stille reaction to provide macrocycle 116.
Scheme 33
Total synthesis of the HIV-1 integrase inhibitor 119 using a Stille reaction to append the carbonylated side-chain to the central pyridine ring.
Scheme 34
Example of an iron-catalyzed Kumada reaction in the synthesis of 122.
Scheme 35
Synthesis of idebenone (124) based on Heck reaction of 2-bromo-3,4,5-trimethoxy-1-methylbenzene with dec-9-en-1-ol under microwave irradiation.
Scheme 36
Synthesis of the ginkgolic acid based on the Heck reaction of aryl triflate 130.
Scheme 37
Heck reaction in synthesis of olopatadine (133) and trans-olopatadine (134).
Scheme 38
Two Heck-based approaches employed in the synthesis of caffeine-styryl derivatives.
Scheme 39
Synthesis of piperidine analogues by Heck reactions.
Scheme 40
Process for axitinib based on palladium catalyzed Migita C-S coupling and Heck reaction.
Scheme 41
Synthesis of (R)-tolterodine based on a Heck-Matsuda reaction and enantioselective reduction of compound 152.
Scheme 42
Heck-Matsuda reaction applied in the synthesis of 158, an intermediate in the synthesis of 154.
Scheme 43
Heck-Matsuda as key step in the syntheses of abamine SG, abamine and naftifine.
Scheme 44
Synthesis of 167 by means of a Heck-Matsuda reaction.
Scheme 45
Double Heck-Matsuda arylation en route to 172.
Scheme 46
Initial model studies for the synthesis of 176.
Scheme 47
Synthesis of 176 by means of a modified Heck-Matsuda procedure.