Page 769 - Advanced Organic Chemistry Part B - Reactions & Synthesis

Scheme 8.14. (Continued) 745
B. Alkenylboranes and alkylboronic acids SECTION 8.2
Reactions Involving
Organopalladium
2 3
3
11 j CH (CH ) H Ph Pd(PPh ) CH (CH ) H Intermediates
3
2 3
O H 3 4 H
H B + Br NaOC H H
O H 2 5
H Ph
86%
12 k
O
)
2 8
3
CH CH 2 B O Br H Pd(PPh 3 4 CH 3 CH 2 H (CH ) OTHP
+ NaOC H H
H H H (CH ) OTHP 2 5
2 8
H H
73%
CH (CH ) CH (CH )
13 l 3 2 5 B(O-i-Pr)2 Pd(PPh ) 3 2 5 Ph
3 4
+ I
H H NaOEt H H
98%
14 m CH OCH 2 (HO) B OSiR 3 Pd(PPh )
3
3 4
O 2
SiO + TlOH
R 3 I OSiR 3 CH OCH
OH R SiO OSiR 3 3 2 OSiR 3
3
3
R SiO R 3 SiO O
R SiO
3
OSiR 3
R SiO R SiO OH R SiO OSiR 3
3
3
3
CH CH CH
15 n 3 3 B(OH) 2 I CH 3 Pd(PPh 3 4 3 CH 3
) ,
+ CO C H 7 mol % 67%
2 2 5
CH 3 TlOH CH 3 CH 3
CO C H
2 2 5
16 o O
CH 3 O (i-Pr) NC
2
O SCF 3 (i-Pr) 2 NC CH 3
3
Pd(PPh ) 80%
3 4
O + (HO) B NaCO , LiCl O
2
3
CH 3 CH 3
CH 3 CH 3
17 p CH 3
CH 3 O (CH ) O CCH Pd(PPh 3 4 (CH 2 ) 2 O 2 CCH 3
) ,
2
3
2 2
I + B 4 mol %
O 62%
OCH 3 NaOH OCH 3
(Continued)