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Communication

Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes

1
Frontier Research Base for Global Young Researchers Center for Open Innovation Research and Education (COiRE), Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
2
Department of Applied Chemistry, Graduate School of Engineering, Osaka University; Osaka 565-0871, Japan
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(8), 1884; https://doi.org/10.3390/molecules23081884
Received: 7 July 2018 / Revised: 26 July 2018 / Accepted: 27 July 2018 / Published: 27 July 2018
(This article belongs to the Special Issue Indium in Organic Synthesis)
Regioselective anti-allylindation of alkynes was achieved using InBr3 and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I2 to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene. View Full-Text
Keywords: indium; allylmetalation; alkyne; allylic silane indium; allylmetalation; alkyne; allylic silane
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MDPI and ACS Style

Nishimoto, Y.; Yi, J.; Takata, T.; Baba, A.; Yasuda, M. Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes. Molecules 2018, 23, 1884. https://doi.org/10.3390/molecules23081884

AMA Style

Nishimoto Y, Yi J, Takata T, Baba A, Yasuda M. Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes. Molecules. 2018; 23(8):1884. https://doi.org/10.3390/molecules23081884

Chicago/Turabian Style

Nishimoto, Yoshihiro, Junyi Yi, Tatsuaki Takata, Akio Baba, and Makoto Yasuda. 2018. "Regio- and Stereoselective Allylindation of Alkynes Using InBr3 and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes" Molecules 23, no. 8: 1884. https://doi.org/10.3390/molecules23081884

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