Title

Synthesis of Boron-Nitrogen Heterocycles via Radical Cyclization of Amine Carboxyborane

Alternative Title

아민 카복시보레인의 라디칼 고리화를 통한 붕소-질소 헤테로 고리 화합물의 합성

DGIST Authors

GI SEYUN ; Sunggi Lee

Advisor

이성기

Issued Date

2026

Awarded Date

2026-02-01

Type

Thesis

Description

Carboxyborane, Ligated boryl radical, Markovnikov hydroboration, 5-exo-trig cyclization, Boron nitrogen containing cyclic compounds, 1,2-azaborolidine

Table Of Contents

Ⅰ. Introduction 1
1.1 Introduction 1

Ⅱ. Results and Discussion 8
2.1 Reaction optimization 8
2.1.1 Solvent screening 8
2.1.2 Photocatalyst screening 9
2.1.3 Base screening 10
2.1.4 Equivalent screening 11
2.1.5 Concentration screening 12
2.2 Substrate scope 13
2.3 Synthesis of starting materials 14
2.4 Mechanistic studies 15
2.4.1 Control experiment 16
2.4.2 Radical inhibition experiment 16
2.4.3 Light on/off experiment 17
2.4.4 Proposed mechanism 18
2.5 Comparison between amine-carboxyborane and amine-borane 18

Ⅲ. Conclusion 19
3.1 Conclusion 19

Ⅳ. Experimental data 20
4.1 Experimental section 20
4.1.1 Preparation of 1-(3-butenyl)amine substrate 20
4.1.2 Preparation of 1-(3-butenyl)amine-carboxyborane substrate 21
4.1.3 Reaction for boron-nitrogen containing cyclic compounds 24
4.1.4 Other compounds 27

Reference 32
요약문 34

URI

https://scholar.dgist.ac.kr/handle/20.500.11750/59735
http://dgist.dcollection.net/common/orgView/200000945303

DOI

10.22677/THESIS.200000945303

Degree

Master

Department

Department of Physics and Chemistry

Publisher

DGIST

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