Chelation- assisted catalytic C- C, C- Si, and C- halogen bond formation by substitution via the cleavage of C(sp2)- H and C(sp3)- H bonds

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Abstract

Catalytic, regioselective C- H functionalizations have been extensively studied over the past two decades. In this account, we report our results on catalytic C- C, C- Si, and C- halogen bond formation reactions by substitution via the cleavage of C- H bonds. Catalytic arylation with arylboronates was developed and applied to the convenient synthesis of polycyclic aromatic hydrocarbons. Alkenylation reactions were also realized by the use of alkenylboronates and alkenyl esters. Various carbonyl- containing substituents were introduced using carbamoyl chlorides, alkyl chloroformates, acyl chlorides, and cyclic alkenyl carbonates. C- Si bonds were formed by reactions with hydrosilanes and vinylsilanes. C- H halogenation reactions were achieved by a combination of C- H bond cleavage and electrochemical oxidation and were applied to one- pot arylation reactions using the Suzuki- Miyaura coupling prodecure.

Original languageEnglish
Pages (from-to)1099-1110
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume73
Issue number11
Publication statusPublished - 2015

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Halogens
Chelation
Chlorides
Alkenylation
Substitution reactions
Halogenation
Electrochemical oxidation
Carbonates
Polycyclic Aromatic Hydrocarbons
Esters
vinylsilane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Chelation- assisted catalytic C- C, C- Si, and C- halogen bond formation by substitution via the cleavage of C(sp2)- H and C(sp3)- H bonds",
abstract = "Catalytic, regioselective C- H functionalizations have been extensively studied over the past two decades. In this account, we report our results on catalytic C- C, C- Si, and C- halogen bond formation reactions by substitution via the cleavage of C- H bonds. Catalytic arylation with arylboronates was developed and applied to the convenient synthesis of polycyclic aromatic hydrocarbons. Alkenylation reactions were also realized by the use of alkenylboronates and alkenyl esters. Various carbonyl- containing substituents were introduced using carbamoyl chlorides, alkyl chloroformates, acyl chlorides, and cyclic alkenyl carbonates. C- Si bonds were formed by reactions with hydrosilanes and vinylsilanes. C- H halogenation reactions were achieved by a combination of C- H bond cleavage and electrochemical oxidation and were applied to one- pot arylation reactions using the Suzuki- Miyaura coupling prodecure.",
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T1 - Chelation- assisted catalytic C- C, C- Si, and C- halogen bond formation by substitution via the cleavage of C(sp2)- H and C(sp3)- H bonds

AU - Kakiuchi, Fumitoshi

AU - Kochi, Takuya

PY - 2015

Y1 - 2015

N2 - Catalytic, regioselective C- H functionalizations have been extensively studied over the past two decades. In this account, we report our results on catalytic C- C, C- Si, and C- halogen bond formation reactions by substitution via the cleavage of C- H bonds. Catalytic arylation with arylboronates was developed and applied to the convenient synthesis of polycyclic aromatic hydrocarbons. Alkenylation reactions were also realized by the use of alkenylboronates and alkenyl esters. Various carbonyl- containing substituents were introduced using carbamoyl chlorides, alkyl chloroformates, acyl chlorides, and cyclic alkenyl carbonates. C- Si bonds were formed by reactions with hydrosilanes and vinylsilanes. C- H halogenation reactions were achieved by a combination of C- H bond cleavage and electrochemical oxidation and were applied to one- pot arylation reactions using the Suzuki- Miyaura coupling prodecure.

AB - Catalytic, regioselective C- H functionalizations have been extensively studied over the past two decades. In this account, we report our results on catalytic C- C, C- Si, and C- halogen bond formation reactions by substitution via the cleavage of C- H bonds. Catalytic arylation with arylboronates was developed and applied to the convenient synthesis of polycyclic aromatic hydrocarbons. Alkenylation reactions were also realized by the use of alkenylboronates and alkenyl esters. Various carbonyl- containing substituents were introduced using carbamoyl chlorides, alkyl chloroformates, acyl chlorides, and cyclic alkenyl carbonates. C- Si bonds were formed by reactions with hydrosilanes and vinylsilanes. C- H halogenation reactions were achieved by a combination of C- H bond cleavage and electrochemical oxidation and were applied to one- pot arylation reactions using the Suzuki- Miyaura coupling prodecure.

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