Efficient One-Pot Synthesis of 2-Carbonyl- 1-indanols by Palladium-Catalyzed Tandem Heck–Aldol Reaction

Abstract

2-Carbonyl-1-indanols were synthesized in moderate to good yields by the reaction of orthohalogenated aryl aldehyde with Morita–Baylis–Hillman adducts via a one-pot, palladium-catalyzed tandem Heck–aldol reaction. Various Morita–Baylis–Hillman adducts were examined to find the scope and limitations of this process.

Keywords:

• 2-carbonyl-l-indanol
• Morita–Baylis–Hillman adducts
• one-pot
• palladium-catalyzed

ACKNOWLEDGMENT

The authors thank Shenyang BMD Chemical Co., Ltd., for financial support of this investigation.

Notes

^a Reaction conditions: 1a (0.5 mmol), 2a (0.6 mmol), TBAB (1.0 mmol), base (1.25 mmol) except for Et₃N (4.0 mmol), Pd(OAc)₂ (5 mol %), and DMF (5 mL).

^b Isolated yields of diastereoisomer mixtures.

^c 1.0 mmol LiCl was added.

^d 10 mol % PPh₃ was added.

^a Reaction conditions: arylhalides 1 (1.0 mmol), Morita-Baylis-Hillman adducts 2 (1.2 mmol), TBAB (2.0 mmol), NaHCO₃ (2.5 mmol), and Pd(OAc)₂ (5 mol %), DMF (10 mL) at 80°C.

^b Ratio of the diastereoisomers was determined by ¹H NMR.

^c Isolated yields of diastereoisomer mixtures.

^d Lower isolated yield due to hard purification of the product from the mixture of starting material 2c and indanol 3c.