Organic Chemistry

472 CHAPTER 12 Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

The Heck reactioncouples an aryl, benzyl, or vinyl halide or triflate (Section 12.4)

with an alkene in a basic solution.

The Stille reactioncouples an aryl, benzyl, or vinyl halide or triflate with a stannane.

Aryl and vinyl groups are coupled preferentially, but an alkyl group can be coupled if

a tetraalkylstannane is used.

The Suzuki reactioncouples an aryl, benzyl, or vinyl halide with an organoborane in

a basic solution.

PROBLEM 35

What alkyl halides would you utilize to synthesize the following compounds, using the

organoborane shown?

B

O

O

an organoborane

CH 2

Br

CH 2

CH 2 CH 2 CH 3

+ CH 3 CH 2 CH 2

+ + NaBr

B

O

O

HO B

O

O

+ HO B + NaBr

O

O

Pd(PPh 3 ) 4

CH 3 Br CH 3 CHCH 3

CH 3 CH CH NaOH

Pd(PPh 3 ) 4

NaOH

+ B

O

O

CH

Suzuki reaction

an aryl halide

an aryl triflate

Pd(PPh 3 ) 4

CCH 3

Br

CH 2 CH 2

(CH 3 CH 2 ) 3 N

Pd(PPh 3 ) 4

(CH 3 CH 2 ) 3 N

+ + HBr

+ HOTf

O

CCH 3

CH CH 2

O

CH 3 O

Heck reaction

OTf

+

CH 3 O

a stannane

CH (^3) THF (CH 3 CH 2 CH 2 CH 2 ) 3 SnBr
Stille reaction
CHSn(CH 2 CH 2 CH 2 CH 3 ) 3
Pd(PPh 3 ) 4
Br CH CH 2

• 
  
  
  
  • THF
    Pd(PPh 3 ) 4
    CH 2 CH 2 CH 2 CH 3
    (CH 3 CH 2 CH 2 CH 2 ) 4 Sn
    OTf
  
  
  
  


• 
  
  
  
  • (CH 3 CH 2 CH 2 CH 2 ) 3 SnOTf
    tetrabutylstannane
    John K. Stillewas a professor of
    chemistry at Colorado State
    University until his untimely death in
    1989 in a commercial air crash on
    his way to a scientific meeting in
    Switzerland.
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