The Experts below are selected from a list of 12 Experts worldwide ranked by ideXlab platform
Qiu Wang - One of the best experts on this subject based on the ideXlab platform.
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synthesis of ortho haloaminoarenes by aryne insertion of Nitrogen Halide bonds
Journal of Organic Chemistry, 2015Co-Authors: Charles E. Hendrick, Qiu WangAbstract:A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of N–X insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
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Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.
Organic Letters, 2013Co-Authors: Charles E. Hendrick, Stacey L. Mcdonald, Qiu WangAbstract:A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a Nitrogen–Halide bond (N–X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.
Charles E. Hendrick - One of the best experts on this subject based on the ideXlab platform.
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synthesis of ortho haloaminoarenes by aryne insertion of Nitrogen Halide bonds
Journal of Organic Chemistry, 2015Co-Authors: Charles E. Hendrick, Qiu WangAbstract:A rapid and general access to ortho-haloaminoarenes has been developed by aryne insertion into N-chloramine, N-bromoamine, and N-iodoamine bonds via two complementary protocols harnessing fluoride-promoted 1,2-elimination of ortho-trimethylsilyl aryltriflates. Typically, electron-deficient N-chloramines effectively react with aryne intermediates generated at elevated temperature with CsF, while less stable N-haloamines are found more efficient under milder, TBAF-mediated aryne formation at room temperature. Both protocols demonstrate a good level of regioselectivity and functional group tolerance. Efforts to elucidate the mechanism of N–X insertion are also discussed. The practical value of this transformation is highlighted by rapid synthesis of novel analogues of the antipsychotic cariprazine.
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Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.
Organic Letters, 2013Co-Authors: Charles E. Hendrick, Stacey L. Mcdonald, Qiu WangAbstract:A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a Nitrogen–Halide bond (N–X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.
Stacey L. Mcdonald - One of the best experts on this subject based on the ideXlab platform.
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Insertion of arynes into N-halo bonds: a direct approach to o-haloaminoarenes.
Organic Letters, 2013Co-Authors: Charles E. Hendrick, Stacey L. Mcdonald, Qiu WangAbstract:A new approach to access o-haloaminoarenes has been achieved by insertion of arynes into a Nitrogen–Halide bond (N–X). This transition-metal-free transformation displays a broad substrate scope of arynes, good compatibility with functional groups, and high regioselectivity. Representative transformations of the o-haloaminoarenes are described to highlight their utility for rapid access to diversely functionalized aminoarene derivatives.
Jonathan A. Ellman - One of the best experts on this subject based on the ideXlab platform.
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Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.
Journal of Organic Chemistry, 2018Co-Authors: Gia L. Hoang, Andrew D. Streit, Jonathan A. EllmanAbstract:An efficient, three-component strategy for Rh(III)-catalyzed annulation of readily available 3-aminopyrazoles, aldehydes, and sulfoxonium ylides to give diverse pyrazolo[1,5-a]pyrimidines is disclosed. The reactions were performed under straightforward benchtop conditions using microwave heating with short reaction times. Good yields were obtained for many substituted aminopyrazoles and a very large variety of aromatic and heteroaromatic aldehydes, including those incorporating electron-withdrawing, electron-donating, basic Nitrogen, Halide and acidic functionality. Ester and methoxy functionalities could also be directly installed on the pyrimidine ring by employing ethyl glyoxylate and trimethyl orthoformate in place of the aldehyde, respectively. In addition, a range of sulfoxonium ylides provided products in good yields to establish that aryl, heteroaryl, and branched and unbranched alkyl substituents can be introduced with this reagent. Finally, the first use of a formyl sulfoxonium ylide in a chemic...
Gia L. Hoang - One of the best experts on this subject based on the ideXlab platform.
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Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrazolo[1,5- a]pyrimidines.
Journal of Organic Chemistry, 2018Co-Authors: Gia L. Hoang, Andrew D. Streit, Jonathan A. EllmanAbstract:An efficient, three-component strategy for Rh(III)-catalyzed annulation of readily available 3-aminopyrazoles, aldehydes, and sulfoxonium ylides to give diverse pyrazolo[1,5-a]pyrimidines is disclosed. The reactions were performed under straightforward benchtop conditions using microwave heating with short reaction times. Good yields were obtained for many substituted aminopyrazoles and a very large variety of aromatic and heteroaromatic aldehydes, including those incorporating electron-withdrawing, electron-donating, basic Nitrogen, Halide and acidic functionality. Ester and methoxy functionalities could also be directly installed on the pyrimidine ring by employing ethyl glyoxylate and trimethyl orthoformate in place of the aldehyde, respectively. In addition, a range of sulfoxonium ylides provided products in good yields to establish that aryl, heteroaryl, and branched and unbranched alkyl substituents can be introduced with this reagent. Finally, the first use of a formyl sulfoxonium ylide in a chemic...