Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction
All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synt...
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| Published in | Nature chemistry Vol. 11; no. 12; pp. 1106 - 1112 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
01.12.2019
Springer Nature Nature Publishing Group |
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| Online Access | Get full text |
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| Abstract | All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene catalysis, which is enabled by a modified norbornene containing a C2 amide moiety. This new norbornene co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system.
All-carbon tetrasubstituted olefins are challenging to prepare in a regio- and stereocontrolled fashion. Now, using an amide-substituted norbornene as a co-catalyst, alkenyl halide- or triflate-mediated palladium/norbornene (Pd/NBE) catalysis has been demonstrated, providing an efficient strategy for modular and regioselective construction of all-carbon tetrasubstituted olefins. |
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| AbstractList | All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene catalysis, which is enabled by a modified norbornene containing a C2 amide moiety. This new norbornene co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system.
All-carbon tetrasubstituted olefins are challenging to prepare in a regio- and stereocontrolled fashion. Now, using an amide-substituted norbornene as a co-catalyst, alkenyl halide- or triflate-mediated palladium/norbornene (Pd/NBE) catalysis has been demonstrated, providing an efficient strategy for modular and regioselective construction of all-carbon tetrasubstituted olefins. All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene catalysis, which is enabled by a modified norbornene containing a C2 amide moiety. This new norbornene co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system. All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene (Pd/NBE) catalysis, which is enabled by a modified NBE containing a C2 amide moiety. This new NBE co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system. All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene catalysis, which is enabled by a modified norbornene containing a C2 amide moiety. This new norbornene co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system.All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled construction of this structural motif still constitutes a significant synthetic challenge. Here, we show that a modular and regioselective synthesis of all-carbon tetrasubstituted olefins can be realized via alkenyl halide- or triflate-mediated palladium/norbornene catalysis, which is enabled by a modified norbornene containing a C2 amide moiety. This new norbornene co-catalyst effectively suppressed undesired cyclopropanation pathways, which have previously been a main obstacle for developing such reactions. Diverse cyclic and acyclic alkenyl bromides or triflates with a wide range of functional groups can be employed as substrates. Various substituents can be introduced at the alkene C1 and C2 positions regioselectively simply by changing the coupling partners. Initial mechanistic studies provide insights on the rate-limiting step as well as the structure of the actual active ligand in this system. |
| Author | Yang, Cheng Wang, Jianchun Dong, Zhe Dong, Guangbin |
| Author_xml | – sequence: 1 givenname: Jianchun orcidid: 0000-0002-3998-8699 surname: Wang fullname: Wang, Jianchun organization: Department of Chemistry, University of Chicago – sequence: 2 givenname: Zhe surname: Dong fullname: Dong, Zhe organization: Department of Chemistry, University of Chicago – sequence: 3 givenname: Cheng surname: Yang fullname: Yang, Cheng organization: Department of Chemistry, University of Chicago – sequence: 4 givenname: Guangbin orcidid: 0000-0003-1331-6015 surname: Dong fullname: Dong, Guangbin email: gbdong@uchicago.edu organization: Department of Chemistry, University of Chicago |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31740759$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
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| DOI | 10.1038/s41557-019-0358-y |
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| Keywords | REAGENTS LIGANDS PALLADACYCLES ARYLATION SEQUENCE C-H FUNCTIONALIZATION ALKYNES SUBSTITUTED ARYL IODIDES CARBOMETALATION PALLADIUM-CATALYZED ALKYLATION |
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| Snippet | All-carbon tetrasubstituted olefins have been found in numerous biologically important compounds and organic materials. However, regio- and stereocontrolled... |
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| SubjectTerms | 639/638/403/933 639/638/549/933 639/638/77/888 Alkenes Analytical Chemistry Biochemistry Bromides Carbon Catalysis Catalysts Chemistry Chemistry and Materials Science Chemistry, Multidisciplinary Chemistry/Food Science Functional groups Inorganic Chemistry Organic Chemistry Organic materials Palladium Physical Chemistry Physical Sciences Regioselectivity Science & Technology Substrates |
| Title | Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction |
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