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Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

ABSTRACT: A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

SUBMITTER: Seiple IB 

PROVIDER: S-EPMC2946225 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

Seiple Ian B IB   Su Shun S   Rodriguez Rodrigo A RA   Gianatassio Ryan R   Fujiwara Yuta Y   Sobel Adam L AL   Baran Phil S PS  

Journal of the American Chemical Society 20100901 38

A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to ac  ...[more]

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