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Transformation of Carbonates into Sulfones at the Benzylic Position via Palladium-Catalyzed Benzylic Substitution

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Ryoichi Kuwano,* Yutaka Kondo, and Tsuyoshi Shirahama

Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan

Org. Lett., 2005, 7 (14), pp 2973–2975

DOI: 10.1021/ol0509787

Publication Date (Web): June 15, 2005

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

The nucleophilic substitution of benzylic carbonates with sodium arenesulfinates was catalyzed by the palladium complex generated in situ from [Pd(η³-C₃H₅)Cl]₂ and DPEphos [bis(2-diphenylphosphinophenyl)ether]. The catalytic reaction proceeded in DMSO at 80 °C and gave a variety of benzylic sulfones in high yields.

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Citing Articles

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Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 11 ACS Journal articles (5 most recent appear below).

Intramolecular S_N′-Type Aromatic Substitution of Benzylic Carbonates at their Para-Position
Satoshi Ueno, Sadakazu Komiya, Takeshi Tanaka, and Ryoichi Kuwano
Organic Letters2012 14 (1), 338-341
- Intramolecular S_N′-Type Aromatic Substitution of Benzylic Carbonates at their Para-Position
  Satoshi Ueno, Sadakazu Komiya, Takeshi Tanaka, and Ryoichi Kuwano
  Organic Letters2012 14 (1), 338-341
  The benzylic carbonates, which connect with an active methine through an o-phenylene tether at their meta-position, are cyclized by Pd(η3-C3H5)Cp–S-Phos catalyst, yielding 3-methyl-9,10-dihydrophenanthrenes. In the catalytic cyclization, the internal ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water
Hidemasa Hikawa and Yuusaku Yokoyama
Organic Letters2011 13 (24), 6512-6515
- Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water
  Hidemasa Hikawa and Yuusaku Yokoyama
  Organic Letters2011 13 (24), 6512-6515
  Palladium-catalyzed benzylation of unprotected anthranilic acids with benzyl alcohols in the presence of Pd(OAc)2 (5 mol %) and sodium diphenylphosphinobenzene-3-sulfonate (TPPMS, 10 mol %) in water at 120 °C for 16 h gave only dibenzylated anthranilic ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Studies on the Synthesis of Apoptolidin: Synthesis of a C₁–C₂₇ Fragment of Apoptolidin D
Madduri Srinivasarao, Youngsoon Kim, Xiaojin Harry Li, Daniel W. Robbins, and Philip L. Fuchs
The Journal of Organic Chemistry2011 76 (19), 7834-7841
- Studies on the Synthesis of Apoptolidin: Synthesis of a C₁–C₂₇ Fragment of Apoptolidin D
  Madduri Srinivasarao, Youngsoon Kim, Xiaojin Harry Li, Daniel W. Robbins, and Philip L. Fuchs
  The Journal of Organic Chemistry2011 76 (19), 7834-7841
  Synthesis of a C1–C27 fragment, a key intermediate in the synthesis of apoptolidin D, is reported. The synthesis involves a combination of Heck coupling and Horner–Wadsworth–Emmons reaction for the C1–C7 trienoate portion and an efficient Suzuki cross-...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions
Jimmie D. Weaver, Antonio Recio, III, Alexander J. Grenning, and Jon A. Tunge
Chemical Reviews2011 111 (3), 1846-1913
- Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions
  Jimmie D. Weaver, Antonio Recio, III, Alexander J. Grenning, and Jon A. Tunge
  Chemical Reviews2011 111 (3), 1846-1913
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Decarboxylative Benzylations of Alkynes and Ketones
Robert R. P. Torregrosa, Yamuna Ariyarathna, Kalicharan Chattopadhyay and Jon A. Tunge
Journal of the American Chemical Society2010 132 (27), 9280-9282
- Decarboxylative Benzylations of Alkynes and Ketones
  Robert R. P. Torregrosa, Yamuna Ariyarathna, Kalicharan Chattopadhyay and Jon A. Tunge
  Journal of the American Chemical Society2010 132 (27), 9280-9282
  Benzyl esters of propiolic and β-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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Published In Issue July 07, 2005
Received April 30, 2005

Select a CAS section from the 5 main topical divisions below:

Letter

Transformation of Carbonates into Sulfones at the Benzylic Position via Palladium-Catalyzed Benzylic Substitution

Abstract

Citing Articles

Intramolecular S_N′-Type Aromatic Substitution of Benzylic Carbonates at their Para-Position

Intramolecular S_N′-Type Aromatic Substitution of Benzylic Carbonates at their Para-Position

Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Palladium-Catalyzed Benzylation of Unprotected Anthranilic Acids with Benzyl Alcohols in Water

Studies on the Synthesis of Apoptolidin: Synthesis of a C₁–C₂₇ Fragment of Apoptolidin D

Studies on the Synthesis of Apoptolidin: Synthesis of a C₁–C₂₇ Fragment of Apoptolidin D

Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions

Transition Metal-Catalyzed Decarboxylative Allylation and Benzylation Reactions

Decarboxylative Benzylations of Alkynes and Ketones