Pd-Catalyzed Cross-Coupling of Acyl Chlorides with In Situ–Generated Alkynylzinc Derivatives for the Synthesis of Ynones

Abstract

A mild and operationally simple procedure by Pd-catalyzed cross-coupling of acyl chlorides with in situ–generated alkynylzinc derivatives was developed, giving the corresponding ynones in good yields.

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GRAPHICAL ABSTRACT

Keywords:

• Acyl chlorides
• alkynylzinc
• Pd-catalyzed
• solvent-free
• ynones

ACKNOWLEDGMENTS

The work was supported by the NCET Foundation, NSFC (30725045), Global Research Network for Medicinal Plants (GRNMP), King Saud University, Shanghai Leading Academic Discipline Project (B906), FP7- PEOPLE-IRSES-2008 (TCMCANCER Project 230232), Key Laboratory of Drug Research for Special Environments, PLA, Shanghai Engineering Research Center for the Preparation of Bioactive Natural Products (10DZ2251300), the Scientific Foundation of Shanghai China (09DZ1975700, 09DZ1971500, 10DZ1971700), and the Twelfth Five-Year National Science and Technology Support Program (2012BAI29B06).

Notes

^a Reaction conditions: acid chloride (1 mmol), 1-alkyne (1 mmol), Pd(PPh₃)₄ (0.5 mol %), ZnCl₂ (1.2 mmol), and Et₃N (2 mmol), 30 min.

^b Isolated yields.

^a Reaction conditions: acid chloride (1 mmol), 1-alkyne (1 mmol), Pd(PPh₃)₄ (0.5 mol %), ZnCl₂ (1.2 mmol), and Et₃N (2 mmol), 30 min.

^b Isolated yields.

^c Use DIEA as base.

^a Reaction conditions: acid chloride (1 mmol), 1-alkyne (1 mmol), Pd catalyst (0.5 mol %), ZnCl₂ or ZnBr₂ (1.2 mmol), and Et₃N (2 mmol), 30 min.

^b Ynones yield/anhydride yield.

^c No catalyst was used.

^d Palimkar's method.

^e No ZnCl₂ or ZnBr₂ was used.