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Molecules 2018, 23(8), 1884; https://doi.org/10.3390/molecules23081884

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.
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)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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.

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