Copper‐Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β‐Borylenones
Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly fun...
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| Published in | Angewandte Chemie International Edition Vol. 57; no. 32; pp. 10328 - 10332 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
06.08.2018
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products.
Four bits: A copper‐catalyzed four‐component coupling reaction of alkynes, alkyl halides, B2pin2, and CO enables modular synthesis of β‐borylated tetrasubstituted enones. The reaction employs readily available feedstocks and proceeds under mild reaction conditions. The utility of this method was demonstrated by various transformations of the borylated products. |
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| AbstractList | Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β-position, using a copper-catalyzed four-component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B
pin
), and CO. A broad scope of highly functionalized β-borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all-carbon tetrasubstituted enones was realized by employing the β-borylated enone unit, without purification, in a Suzuki-Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B 2 pin 2 ), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β-position, using a copper-catalyzed four-component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2 pin2 ), and CO. A broad scope of highly functionalized β-borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all-carbon tetrasubstituted enones was realized by employing the β-borylated enone unit, without purification, in a Suzuki-Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products.Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β-position, using a copper-catalyzed four-component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2 pin2 ), and CO. A broad scope of highly functionalized β-borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all-carbon tetrasubstituted enones was realized by employing the β-borylated enone unit, without purification, in a Suzuki-Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the beta-position, using a copper-catalyzed four-component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B(2)pin(2)), and CO. A broad scope of highly functionalized beta-borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all-carbon tetrasubstituted enones was realized by employing the beta-borylated enone unit, without purification, in a Suzuki-Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products. Four bits: A copper‐catalyzed four‐component coupling reaction of alkynes, alkyl halides, B2pin2, and CO enables modular synthesis of β‐borylated tetrasubstituted enones. The reaction employs readily available feedstocks and proceeds under mild reaction conditions. The utility of this method was demonstrated by various transformations of the borylated products. |
| Author | Mankad, Neal P. Cheng, Li‐Jie |
| Author_xml | – sequence: 1 givenname: Li‐Jie surname: Cheng fullname: Cheng, Li‐Jie organization: University of Illinois at Chicago – sequence: 2 givenname: Neal P. orcidid: 0000-0001-6923-5164 surname: Mankad fullname: Mankad, Neal P. email: npm@uic.edu organization: University of Illinois at Chicago |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29846998$$D View this record in MEDLINE/PubMed |
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| Keywords | multicomponent reactions PAUSON-KHAND REACTION ALKYNYLBORATION alkynes CARBOBORATION ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS IODIDES BORATION BIS(PINACOLATO)DIBORON copper RADICALS STEREOSELECTIVE-SYNTHESIS boron synthetic methods CYCLIZATION |
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| Snippet | Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling... Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the beta-position, using a copper-catalyzed four-component... Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β-position, using a copper-catalyzed four-component coupling... |
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| SubjectTerms | Alcohols Alkynes boron Chemistry Chemistry, Multidisciplinary Copper Coupling Halides Halogenation multicomponent reactions Organic chemistry Organic compounds Oxidation Physical Sciences Purification Science & Technology Synthesis synthetic methods |
| Title | Copper‐Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β‐Borylenones |
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