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

125 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

Bibliographical note

Funding Information:
Financial support was provided by the NSF (CHE-1665125) and University of North Carolina. C.C.R. is an NSF graduate research fellow. We are grateful to M. Brookhart for helpful discussions and R. Sommer for assistance obtaining the X-ray structure of 19.

Publisher Copyright:
© 2017 American Chemical Society.

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10.1021/jacs.7b08575

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

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.",

author = "Marcum, \{Justin S.\} and Roberts, \{Courtney C.\} and Manan, \{Rajith S.\} and Cervarich, \{Tia N.\} and Meek, \{Simon J.\}",

note = "Funding Information: Financial support was provided by the NSF (CHE-1665125) and University of North Carolina. C.C.R. is an NSF graduate research fellow. We are grateful to M. Brookhart for helpful discussions and R. Sommer for assistance obtaining the X-ray structure of 19. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/jacs.7b08575",

language = "English (US)",

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T1 - Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles

AU - Marcum, Justin S.

AU - Roberts, Courtney C.

AU - Manan, Rajith S.

AU - Cervarich, Tia N.

AU - Meek, Simon J.

N1 - Funding Information: Financial support was provided by the NSF (CHE-1665125) and University of North Carolina. C.C.R. is an NSF graduate research fellow. We are grateful to M. Brookhart for helpful discussions and R. Sommer for assistance obtaining the X-ray structure of 19. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/11/8

Y1 - 2017/11/8

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85033227064

UR - https://www.scopus.com/pages/publications/85033227064#tab=citedBy

U2 - 10.1021/jacs.7b08575

DO - 10.1021/jacs.7b08575

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EP - 15583

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

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

Abstract

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