C-C bond formation via C-H bond activation: Catalytic arylation and alkenylation of alkane segments

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13372-13373

  Sezen, Bengü ^a   Franz, Roberto ^a   Sames, Dalibor ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CARBON; FUNCTIONAL GROUP; HYDROGEN; METAL COMPLEX; OXIDIZING AGENT; PALLADIUM; SCHIFF BASE; SOLVENT; TELEOCIDIN;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

ALKANES; ALKENES; CATALYSIS; HYDROCARBONS, AROMATIC; TOLUIDINES;

EID: 0037073170     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027891q     Document Type: Article

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23. Formation of putative intermediate 3 (and ultimately product 4) may occur via an alternative route wherein the cyclopalladation takes place first, followed by transmetalation (the order of steps 1 and 2 is reversed, Figure 2). This was ruled out as the corresponding palladacycle acetate (not shown) did not afford the product under reaction conditions.
24. In addition to the desired products and biphenyl, there were no other products formed. The starting material was recovered to yield a satisfactory mass balance (∼90%).
25. It is also conceivable that the double bond or phenyl ring of the product coordinates to the metal, thus preventing subsequent functionalization.