Transition metal promoted reactions. 38. NiCl2 (dppe)-catalyzed geminal dialkylation of dithioacetals and trimethylation of ortho thioesters

YL Tzeng, PF Yang, NW Mei, TM Yuan…

Index: Tzeng, Yih-Ling; Yang, Ping-Fan; Mei, Nai-Wen; Yuan, Tien-Min; Yu, Chun-Chi; Luh, Tien-Yau Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 5289 - 5293

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Citation Number: 25

Abstract

NiClp (dppe)-catalyzed cross-coupling of cinnamaldehyde dithioacetab gave the corresponding geminal dimethylation products in excellent yields. Allylic ortho thioesters afforded regioeelectively the corresponding trimethylation products. The reaction may occur via an lselectron r-allyl intermediate, which undergoes facile reductive elimination to afford the geminal dimethylation product. Benzylic dithioacetals having an ortho amino group ...