7. Greg Fu and coworkers found that efficiency of Suzuki-Miyaura coupling with aryl chlorides is highly sensitive to the phosphine ligand used in the catalyst (see figures below). (Note: Pd2(dba); is a commonly- used source of Pdº.) Pdadba), 1.5 mo%, ligand 3.6 mol, Coco, Me (HO)e dioxane, 80 C, 5h 90 80 70 60 * 50 30 20 10 PPhs dppf P(o-tol)a dppp dcype PIt-Bu) cone angle ( P (RPH) 145 27 (a) Why does P(o-tol); provide a more active catalyst than PPh3? (b) Why do PCy; and P(t-Bu); provide more active catalysts than P(o-tol):? 182 (194 ) 11.4 194 (s) paA none BINAP

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7. Greg Fu and coworkers found that efficiency of Suzuki-Miyaura coupling with aryl chlorides is highly
sensitive to the phosphine ligand used in the catalyst (see figures below). (Note: Pd2(dba); is a commonly-
used source of Pd°.)
Pda(dba)s 1.5 mol%,
ligand 3.6 mol%,
Me
(HO);8
dioxane, 80 C, 5h
90
80
Mer
70
60
50
40
30
20
10
PPhs
dppf
Plo-tol)s
dppp
dcype
P(t-Bu)a
cone angle (0):
pK, (RPH+)
Me
145
2.7
170
9.7
(a) Why does P(o-tol): provide a more active catalyst than PPh3?
(b) Why do PCY3 and P(t-Bu); provide more active catalysts than P(o-tol):?
182 (194 )
11.4
194
none
BINAP
Transcribed Image Text:7. Greg Fu and coworkers found that efficiency of Suzuki-Miyaura coupling with aryl chlorides is highly sensitive to the phosphine ligand used in the catalyst (see figures below). (Note: Pd2(dba); is a commonly- used source of Pd°.) Pda(dba)s 1.5 mol%, ligand 3.6 mol%, Me (HO);8 dioxane, 80 C, 5h 90 80 Mer 70 60 50 40 30 20 10 PPhs dppf Plo-tol)s dppp dcype P(t-Bu)a cone angle (0): pK, (RPH+) Me 145 2.7 170 9.7 (a) Why does P(o-tol): provide a more active catalyst than PPh3? (b) Why do PCY3 and P(t-Bu); provide more active catalysts than P(o-tol):? 182 (194 ) 11.4 194 none BINAP
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