Bis-Functionalization of 1,3-Dienes through 1,4-Conjugate Addition of Amphiphilic Bis-π-Allyl and Related Palladium Intermediates

T. V. Baiju; Ajesh Vijayan; Nayana Joseph; Preethanuj Preethalayam; K. V. Radhakrishnan; E. Suresh; Yoshinori Yamamoto

doi:10.1055/s-0033-1340171

Synlett, Table of Contents

Synlett 2014; 25(3): 359-364
DOI: 10.1055/s-0033-1340171

letter

Bis-Functionalization of 1,3-Dienes through 1,4-Conjugate Addition of Amphiphilic Bis-π-Allyl and Related Palladium Intermediates

Authors

T. V. Baiju

^aAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110001, India

^bOrganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India Fax: +91(471)2491712 Email: radhu2005@gmail.com
Ajesh Vijayan

^aAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110001, India

^bOrganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India Fax: +91(471)2491712 Email: radhu2005@gmail.com
Nayana Joseph

^bOrganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India Fax: +91(471)2491712 Email: radhu2005@gmail.com
Preethanuj Preethalayam

^bOrganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India Fax: +91(471)2491712 Email: radhu2005@gmail.com
K. V. Radhakrishnan*

^aAcademy of Scientific and Innovative Research (AcSIR), New Delhi 110001, India

^bOrganic Chemistry Section, National Institute for Interdisciplinary Science and Technology (CSIR), Trivandrum 695019, India Fax: +91(471)2491712 Email: radhu2005@gmail.com
E. Suresh

^cCentral Salt and Marine Chemicals Research Institute, CSIR-CSMCRI, Bhavnagar 364021, Gujarat, India
Yoshinori Yamamoto*

^dWPI-AIMR (Advanced Institute for Materials Research), Tohoku University, Katahira 2-1-1, Aobaku, Sendai 980-8577, Japan Email: yoshi@mail.tains.tohoku.ac.jp

Abstract

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Abstract

Palladium-catalyzed three-component coupling of allylstannane, allyl chloride and a functionalized diene is described. Regioselective 1,4-functionalization of the Michael acceptor 1,3-diene is accomplished by the amphiphilic bis-π-allylpalladium complex. To the best of our knowledge, this is the first time a functionalized 1,3-butadiene has been used as a Michael acceptor. The scope of the present strategy is further extended to 1,4-allylation–oxyallylation of functionalized dienes.

Key words

palladium - allylation - allyl complexes - coupling - Michael addition

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References

References and Notes

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21 Typical Procedure (Compound 4a): To a degassed solution of [PdCl₂(PPh₃)₂] (4.4 mg, 0.0064 mmol) in anhydrous THF (2 mL) in a Schlenk tube, allyltributyl-stannane 3 (85.2 mg, 0.25 mmol) was added followed by allyl chloride 2 (19.6 mg, 0.25 mmol). To this, 1a (42.02 mg, 0.12 mmol) was added (in THF) and the mixture was stirred at room temperature for 8 h. After the completion of the reaction (as evident by TLC), the solvent was removed under reduced pressure and the residue was purified by using silica gel (100–200 mesh) column chromatography (EtOAc–hexane, 12%) to afford 4a (41.1 mg, 78%).
22 Spectral Data of 4a: R_f = 0.46 (EtOAc–hexane, 4:6); IR (neat): 3079, 2955, 2919, 2850, 2313, 2246, 1734, 1604, 1510, 1461, 1376, 1290, 1248, 1177, 1118, 1032 cm^–1; ¹H NMR (500 MHz, CDCl₃): δ = 7.26–7.24 (m, 1 H), 7.08 (d, J = 8.5 Hz, 1 H), 6.98–6.94 (m, 2 H), 5.94–5.86 (m, 1 H), 5.56–5.47 (m, 1 H), 5.42–5.35 (m, 2 H), 5.05–4.98 (m, 2 H), 3.89 (s, 3 H), 3.84 (s, 3 H), 3.72 (s, 3 H), 3.18–3.15 (m, 1 H), 2.87–2.75 (m, 2 H), 2.63–2.58 (m, 1 H), 2.27–2.21 (m, 1 H); ¹³C NMR (125 MHz, CDCl₃): δ = 171.0, 166.0, 160.4, 137.4, 136.6, 134.0, 131.1, 130.1, 128.7, 126.0, 123.5, 118.1, 114.5, 114.3, 113.7 (2C), 55.3, 52.6, 52.5, 48.2, 42.7, 42.5, 33.8; HRMS (ESI): m/z [M + Na]⁺ calcd for C₂₃H₂₄N₂NaO₅: 431.15829; found: 431.15646.
23 CCDC-933875.

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