Group Meeting Problems - 2022/05/07

1
O OCH3 O OH
O
h
O
OCH3
O cyclohexane, rt
H OH H O
90%

G. Majetich et al., Org. Lett., 10, 89 (2008)

 Group Meeting Problems - 2022/05/07

2
Me Me
Me Me
Me IBX (5.0 eq.) Me
H OH OH DMSO, 80 °C H O

H then NaHCO3 H
O Na2S2O3, 25 °C O
Me Me
72%

C.-C. Li et al., J. Am. Chem. Soc., 141, 15773 (2019)

 Group Meeting Problems - 2022/05/14

Q3
N
O
O N Ts
MeO N
7 N Ph 10 mol% PtCl2/L1 10 mol% Au(Ⅲ)2 N
+ MeO N Bn
MeO
Bn toluene, 70 °C Ph DCE, 70 °C
6 N N O
Bn Ph
Ts 90% N 70%
(C6:C7 = 6:1) Ts

P O

MeO N OMe
Ad CF3 AuCl3
3
L1 Au(Ⅲ)2
Ad = 1-adamantyl
A. S. K. Hashmi et al., Nat. Commun., 13, 1672 (2022)
 Group Meeting Problems - 2022/05/14
4
O D O O
[Rh(nbd)2Cl]2 (cat.) Me H2SO4 (cat.) Me
Me Me Me
N Ph PPh3 (cat.) N NaN3 N
D
Me O
1,4-dioxane, 150 °C O TFA, 0 °C to rt
D Ph
78% Ph 64% N

*nbd = norbornadiene

T. Xu et al., Nat. Commun, 12, 3022 (2021)

 Group Meeting Problems - 2022/05/21

5
O
TEMPO (3.8 eq.)
MS4Å Ph O
H2N n-C5H11 n-C5H11
1,4-dioxane, 120 °C N
Ph
86%

W. Su et al., Angew. Chem. Int. Ed., ASAP

DOI : 10.1002/anie.202203365
 Group Meeting Problems - 2022/05/28

R=H Me
Me EtO2C
Pd(dba)2 (5 mol%)
Ligand (10 mol%)
• Me
Me Si
Si + toluene, 80 °C, 12 h Me
Me
R CO2Et
92%
Me
Me
A

F3C CF3

F3C P CF3 Me
Me
R = Me
EtO2C
PtCl2 (8 mol%)
Me
CF3 CF3 toluene, 80 °C, 12 h Si
Me
Ligand
71%

Me
B

Z. Song et al., ACS Catal., 12, 5185 (2022)