Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

Tao Jia; Marshall J. Smith; Alexander P. Pulis; Gregory J. P. Perry; David J. Procter

doi:10.1021/acscatal.9b01911

Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

Tao Jia, Marshall J. Smith, Alexander P. Pulis, Gregory J. P. Perry, David J. Procter

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Abstract

A multicomponent copper-catalyzed enantio- and regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation.

Original language	English
Pages (from-to)	6744-6750
Journal	ACS Catalysis
Early online date	28 Jun 2019
DOIs	https://doi.org/10.1021/acscatal.9b01911
Publication status	Published - 2019

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http://pubs.acs.org/doi/10.1021/acscatal.9b01911

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title = "Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes",

abstract = "A multicomponent copper-catalyzed enantio- and regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation.",

author = "Tao Jia and Smith, {Marshall J.} and Pulis, {Alexander P.} and Perry, {Gregory J. P.} and Procter, {David J.}",

year = "2019",

doi = "10.1021/acscatal.9b01911",

language = "English",

pages = "6744--6750",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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T1 - Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

AU - Jia, Tao

AU - Smith, Marshall J.

AU - Pulis, Alexander P.

AU - Perry, Gregory J. P.

AU - Procter, David J.

PY - 2019

Y1 - 2019

N2 - A multicomponent copper-catalyzed enantio- and regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation.

AB - A multicomponent copper-catalyzed enantio- and regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation.

U2 - 10.1021/acscatal.9b01911

DO - 10.1021/acscatal.9b01911

M3 - Article

SN - 2155-5435

SP - 6744

EP - 6750

JO - ACS Catalysis

JF - ACS Catalysis

ER -

Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes

Abstract

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