Group Meeting Problems - 2021/10/02

allyl acetate
1 NHEt h H
Pd(OAc)2, PPh3
K2CO3
O
NHEt
N H
EtHN
O MeCN, rt THF, 70 °C
N
O N
56% 52%

Kevin I. Booker-Milburn et al., Angew. Chem. Int. Ed., 52, 1499 (2013)
Kevin I. Booker-Milburn et al., Org. Lett., 23, 4986 (2021)
 Group Meeting Problems - 2021/10/02

2 O2
Acridine red (10 mol%)
N Bz
40 W blue LEDs O H
N + TMSN3 O
Bz PhSeSePh (1 eq.)
MeCN, rt; N3
2.0 eq. 4.0 eq. Et3N N
Bz
67% (dr = >20:1)

S.-J. Ji et al., Adv. Synth. Catal., 362, 3131 (2020)

H
O N
Me
Me
N
H
Acridine red
 Group Meeting Problems - 2021/10/09

3 Ts
Na
S Me3OBF4 N Ts • 3 H2O (2.0 eq.) N
CH2Cl2, 23 °C; Cl
Ph OMe Ph OMe
Et3N MeCN/HFIP (9/1), 23 °C
O O

M. Podewitz and T. Maguaer et al., J. Am. Chem. Soc., 143, 9002 (2021)
 Group Meeting Problems - 2021/10/09

4
Ph
Ph
O O
In(OTf)3 (5 mol%)
H
PhCl, 80 C
O
84% O H

P. H. Y. Cheong and Y. R. Lee et al., ACS Catal., 11, 6467 (2021)

 Group Meeting Problems - 2021/10/16

6
Ns O
H O AlCl3
Bn N (0.4 eq.) Ns
N
toluene Bn
Me 105 °C
H Me
68%

R. Hsung et al., J. Am. Chem. Soc., 137, 5596 (2015)

 Group Meeting Problems - 2021/10/23

8
O
Me F
F I N BF3·OEt2 (0.3 eq.)

O DCM/MeNO 2, rt
Me NHTs N
Ts
91% (dr = 20 1

C. Zhang et al., Angew. Chem. Int. Ed., 60, 24171 (2021)

 Group Meeting Problems - 2021/10/30

9
OTMS Rh2(Oct)4 (cat.)
CHO OTMS
MS3A
TsN3, CuTc (cat.) PhMe, 90 °C;
OTMS
O
PhMe, 25 °C Al2O3, CH2Cl2, 25 °C
TMSO
91% 70% CHO

C. -C. Li et al., Org. Lett., 23, 7771 (2021)