Page 770 - Advanced Organic Chemistry Part B - Reactions & Synthesis

746 Scheme 8.14. (Continued)

CHAPTER 8 18 q I Pd(PPh ) ,
3 4
CH O C + 7 mol %
2
3
Reactions Involving BR
Transition Metals OTBDMS 2 (CH ) CH 3
2 3
R = 3-methyl-2-butyl OTBDMS
CH O C
3
2
OTBDMS
(CH ) CH 3
2 3
OTBDMS
76%
19 r S TBDMSO OTPS
CH 3 CH 3 I CH(OCH ) Pd(dppf) ,
2
N + B 3 2 Ph As
3
CH 3
O CCH 3 CH 3 CH 3 CH 3 Cs CO 3
2
2
S TBDMSO OTPS
CH 3 CH 3
3 2
N CH(OCH )
CH 3
O CCH 3 CH 3 CH 3 CH 3 72%
2
CH 3
20 s CH 3 CH 3 Pd(PPh ) CH 3
O 3 CH O O
CH O I + (HO) B TlOH 3
3
OSiEt 3 2 OSiEt 3
C. Alkyl–aryl coupling
3 4
21 t Pd(PPh ) ,
2 mol % PhO(CH )
PhO(CH ) B + CF SO 3 OCH 3 2 3 OCH 3
2 3
3
K PO 4
3
92%
22 u I
CH (CH ) B + O Pd(dppf)Cl , CH (CH ) O
2
3
2 7
3
2 7
3 mol %
O O
NaOCH 3
78%
23 v OCH 3 OCH 3
Pd(dppf)Cl
CH (CH ) B + I 2 (CH ) CH 3
2 7
2 7
3
NaOH
90%
24 w CH 2
B Br Pd(PPh )
3 4
+ CH 2 SPh
PhS K CO 3
2
73 – 81%
25 x Pd (dba) 3 CH CH CH
2
B(OH) + BrCH CH CH K CO 3 2
2
2
2
73%
(Continued)