Synthesis and Application of Conjugated Polyene Molecules by a Direc pi-Expansion Reaction

2021 Fiscal Year Final Research Report

• Project/Area Number: 17H03051
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Tokyo University of Agriculture and Technology
• Principal Investigator: Hirano Masafumi 東京農工大学, 工学(系)研究科(研究院), 教授 (70251585)
• Project Period (FY): 2017-04-01 – 2022-03-31
• Keywords: 交差二量化 / 合成ビルディングブロック / 天然物の合成 / 有機半導体物質

Outline of Final Research Achievements

In this study, a novel catalytic reaction between conjugated dienes and alkynes catalyzed by Ru(0) complexes to form conjugated trienes and tetraenes was established. In particular, following reactions between the boron-substituted conjugated dienes and alkynes, cross-coupling reactions led to the total synthesis of the marine natural product Navenone B and the formal synthesis of the apoptosis control molecule Bongkrekic acid. In addition, a novel method for the synthesis of polysubstituted pyrroles was discovered, in which the reaction of an iminoalkyne with a conjugated diene leads to the formation of a conjugated triene with a nitrogen substituent followed by aromatization. The reaction was also found to be effective for the π-conjugation extension of organic semiconducting materials and other materials.

Free Research Field

分子触媒化学

Academic Significance and Societal Importance of the Research Achievements

本研究は学術的には新規な共役ポリエン、非共役ポリエン分子の構築法を確立するとともにホウ素などの反応性置換基を導入してその合成的有用性を実現し、実際に天然物や電子材料などの合成に適用した。国際的学術誌に合計13報の論文発表をおこなった。また、２件の特許出願を行いJSTの支援によりいずれも各国移行を伴う国際特許となった。学生や一般社会人に向けた化学雑誌への掲載２件、化学ポータルサイトChem-Stationへの掲載２件、新聞報道4件、本研究に関わる企業との共同研究１件、国際共同研究３件など社会的、国際的にも意義ある研究を実施した。