Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Justin S. Marcum; Courtney C. Roberts; Rajith S. Manan; Tia N. Cervarich; Simon J. Meek

doi:10.1021/jacs.7b08575

Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

Justin S. Marcum, Courtney C. Roberts, Rajith S. Manan, Tia N. Cervarich, Simon J. Meek

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

Abstract

Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η³-allyl.

Original language	English (US)
Pages (from-to)	15580-15583
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	44
DOIs	https://doi.org/10.1021/jacs.7b08575
State	Published - Nov 8 2017
Externally published	Yes

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Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles. / Marcum, Justin S.; Roberts, Courtney C.; Manan, Rajith S.; Cervarich, Tia N.; Meek, Simon J.

In: Journal of the American Chemical Society, Vol. 139, No. 44, 08.11.2017, p. 15580-15583.

Research output: Contribution to journal › Article › peer-review

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abstract = "Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.",

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AU - Roberts, Courtney C.

AU - Manan, Rajith S.

AU - Cervarich, Tia N.

AU - Meek, Simon J.

PY - 2017/11/8

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AB - Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.

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Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

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