A Novel Silver Iodide Catalyzed Sonogashira Coupling Reaction

Pinhua Li; Lei Wang

doi:10.1055/s-2006-949640

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Synlett 2006(14): 2261-2265
DOI: 10.1055/s-2006-949640

LETTER

A Novel Silver Iodide Catalyzed Sonogashira Coupling Reaction

Pinhua Li^a, Lei Wang*^a,b
^a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;

Further Information

Publication History

Received 10 February 2006
Publication Date:
24 August 2006 (online)

Abstract
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Abstract

A novel and efficient Ag-catalyzed Sonogashira coupling reaction has been developed. Terminal alkynes couple with aryl iodides and aryl bromides in the presence of silver iodide, triphenylphosphine and potassium carbonate to afford the corresponding cross-coupling products in high yields.

Key words

silver iodide - Sonogashira coupling reactions - terminal alkynes - aryl iodides - aryl bromides

References and Notes

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20

The unique Sonogashira coupling products were characterized by mp, ¹H NMR and ¹³C NMR, and MS.
(4-Acetylphenyl)phenylacetylene: mp 95-96 °C (Lit.²⁴ 94-96 °C). ¹H NMR (250 MHz, CDCl₃): δ = 7.91 (d, J = 8.41 Hz, 2 H), 7.58 (d, J = 8.41 Hz, 2 H), 7.52-7.54 (m, 2 H), 7.33-7.36 (m, 3 H), 2.57 (s, 3 H). ¹³C NMR (62.5 MHz, CDCl₃): δ = 197.1, 136.1, 131.7, 131.6, 128.7, 128.4, 128.2, 128.1, 122.6, 92.6, 88.6, 26.5. MS (relative intensity, %): m/z = 220 (60) [M⁺], 205 (100), 176 (48), 151 (18), 102 (10), 88 (19).
(4-Cyanophenyl)phenylacetylene: mp 109-110 °C (Lit.²⁵ 108.5-109.5 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.59-7.66 (m, 4 H), 7.53-7.57 (m, 2 H), 7.36-7.40 (m, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 132.0 (2 × C), 131.8, 129.1, 128.5, 128.2, 122.2, 118.5, 111.4, 93.7, 87.7. MS: (relative intensity, %): m/z = 203 (100) [M⁺], 176 (8), 151 (5), 75 (5).
(3-Cyanophenyl)phenylacetylene: mp 69-71 °C (Lit.²⁵ 70-71 °C). ¹H NMR (300 MHz, CDCl₃): δ = 7.79 (t, J = 1.50 Hz, 1 H), 7.73 (dt, J = 1.50, 7.80 Hz, 1 H), 7.59 (dt, J = 1.50, 7.80 Hz, 1 H), 7.52-7.55 (m, 2 H), 7.45 (t, J = 7.80 Hz, 1 H), 7.35-7.39 (m, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 135.6, 134.8, 131.7, 131.3, 129.2, 128.9, 128.4, 124.8, 122.2, 118.0, 112.8, 91.7, 86.8. MS (relative intensity, %): m/z = 203 (100) [M⁺], 176 (7), 151 (5), 75 (5).