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One-Pot Synthesis of Diarylalkynes Using Palladium-Catalyzed Sonogashira Reaction and Decarboxylative Coupling of sp Carbon and sp² Carbon

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Jeongju Moon,^† Miso Jeong,^† Hyungoog Nam,^† Jinhun Ju,^† Joong Ho Moon,^‡ Hyun Min Jung,^§ and Sunwoo Lee*^†

Department of Chemistry, Chonnam National University, 300 Yongbong-dong, Buk-gu, Gwangju, 500-757, Republic of Korea, ICx Nomadics, Inc., 215 First Street, Suite 105, Cambridge, Massachusetts 02142, and Advanced Materials Division, Korea Research Institute of Chemical Technology, 100 Jang-dong, Yuseong-gu, Daejeon, 305-600, Republic of Korea

Org. Lett., 2008, 10 (5), pp 945–948

DOI: 10.1021/ol703130y

Publication Date (Web): January 30, 2008

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

Decarboxylative coupling of sp-sp² carbons is possible by palladium catalyst. Employing propiolic acid (1) as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and the decarboxylative coupling, unsymmetrically substituted diaryl alkynes were obtained in moderate to good yield.

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Citing Articles

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This article has been cited by 27 ACS Journal articles (5 most recent appear below).

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  The Journal of Organic Chemistry2011 76 (21), 8621-8628
  A general scheme for the synthesis of π-conjugated molecules based on 3,4-dioxypyrroles is presented. The π-conjugated molecules were synthesized via Pd-mediated decarboxylative cross-coupling using various 3,4-propylenedioxypyrrole carboxylic acids and ...
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Palladium-Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides
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Organic Letters2011 Article ASAP
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  A palladium-catalyzed decarboxylative cross-coupling of potassium 2- and 4-nitrophenyl acetates with aryl chlorides and bromides has been developed. Because the nitro group can be readily converted to many other functional groups, the new reaction ...
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One-Pot Synthesis of Symmetrical and Unsymmetrical Aryl Sulfides by Pd-Catalyzed Couplings of Aryl Halides and Thioacetates
Namjin Park, Kyungho Park, Mihee Jang, and Sunwoo Lee
The Journal of Organic Chemistry2011 Article ASAP
- One-Pot Synthesis of Symmetrical and Unsymmetrical Aryl Sulfides by Pd-Catalyzed Couplings of Aryl Halides and Thioacetates
  Namjin Park, Kyungho Park, Mihee Jang, and Sunwoo Lee
  The Journal of Organic Chemistry2011 Article ASAP
  Aryl sulfides were obtained from the coupling reaction of S-aryl (or S-alkyl) thioacetates and aryl bromides in the presence of palladium catalyst. This reaction method enables the one-pot synthesis of symmetrical and unsymmetrical diaryl sulfides by ...
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Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO₂
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Organic Letters2011 13 (9), 2402-2405
- Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO₂
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  Organic Letters2011 13 (9), 2402-2405
  A convenient approach to selectively prepare a wide range of functionalized propiolic acids was developed by AgI-catalyzed carboxylation of terminal alkynes using carbon dioxide as carboxylative agent under ligand-free conditions.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature
Mingzong Li, Cong Wang, and Haibo Ge
Organic Letters2011 13 (8), 2062-2064
- Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature
  Mingzong Li, Cong Wang, and Haibo Ge
  Organic Letters2011 13 (8), 2062-2064
  A novel Pd-catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with α-oxocarboxylic acids is performed at room temperature. This reaction provides an efficient access to aryl ketones under mild conditions.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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Published In Issue March 06, 2008
Received December 30, 2007

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

Letter

One-Pot Synthesis of Diarylalkynes Using Palladium-Catalyzed Sonogashira Reaction and Decarboxylative Coupling of sp Carbon and sp² Carbon

Abstract

Citing Articles

Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles via Pd-Mediated Decarboxylative Cross-Coupling

Synthesis of π-Conjugated Molecules Based on 3,4-Dioxypyrroles via Pd-Mediated Decarboxylative Cross-Coupling

Palladium-Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides

Palladium-Catalyzed Decarboxylative Coupling of Potassium Nitrophenyl Acetates with Aryl Halides

One-Pot Synthesis of Symmetrical and Unsymmetrical Aryl Sulfides by Pd-Catalyzed Couplings of Aryl Halides and Thioacetates

One-Pot Synthesis of Symmetrical and Unsymmetrical Aryl Sulfides by Pd-Catalyzed Couplings of Aryl Halides and Thioacetates

Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO₂

Ligand-Free Ag(I)-Catalyzed Carboxylation of Terminal Alkynes with CO₂

Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature