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1st October 2014 @ 10:06

Palladium catalysed coupling of JU 26 and JU 29-1 (boronic ester) to form the fluoroalkene.  

Github issue:

Literature ref:

Reaction Scheme

Procedure

Started 4:30pm

JU 26 (~20-30 mg, flask was washed out, 0.1-0.15 mmol, 1 equiv), JU 29-1 (85 mg, 0.3 mmol, 2 equiv), potassium carbonate (104 mg, 0.75 mmol, 6 equiv) were stirred into toluene (3.75 mL), ethanol (0.75 mL) and water (0.75 mL). 2 balloons of argon were bubbled through to remove oxygen. 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride (12 mg, 0.02 mmol, 0.2 equiv) was added and the mixture heated at reflux overnight. 

 

HIRAC

HIRAC JU 31-1.pdf

InChI strings

InChI=1S/C11H15BBrNO2/c1-10(2)11(3,4)16-12(15-10)8-6-5-7-9(13)14-8/h5-7H,1-4H3

and

InChI=1S/C8H6BrF/c9-8(10)6-7-4-2-1-3-5-7/h1-6H/b8-6-

to

InChI=1S/C13H9BrFN/c14-13-8-4-7-12(16-13)11(15)9-10-5-2-1-3-6-10/h1-9H/b11-9-

SMILES

BrC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=N1

and

BrC(F)=[S=I]CC[4]=CC=CC=C@5

to

BrC1=CC=CC(/C(F)=C/C2=CC=CC=C2)=N1

Attached Files
Reaction Scheme JU 31-1.png
HIRAC JU 31-1.pdf