Contents

Contents        1

Reactions        3

Coupling reactions        3

Palladium（Pd）        3

Nikkel（Ni）        12

Reactions with metal reagents        13

Magnesium（Mg、Grinard reagents）        13

Lithium（Li）        15

Calcium（Ca）        16

Barium（Ba）        17

Manganese（Mn）        18

Reductions        19

Birch reduction        19

Nito group reduction        22

Phosphine oxide reduction        23

Radical reactions        24

Fluorination reactions        26

Compounds        27

Heterocyclic compounds（N・O・S）        27

Contains N        27

Contains O・S        29

Amines        31

Polycyclic aromatic hydrocarbons        33

Halogen compounds        36

Fluorine（F）        36

Chlorine（Cl）,Bromine（Br）,Iodine（I）        38

Organic phosphorus compounds        39

Organometallic reagents（Contains boron, silicon as metalloids）        40

Gringnard reagents（Mg）        40

Lithium reagents（Li）        41

Calcium reagents（Ca）        42

Barium reagents（Ba）        43

Manganese reagents（Mn）        44

Organoboron compounds（B）        45

Organosilicon compounds（Si）        46

Reactions

Coupling reactions

Pd触媒反応Palladium

Suzuki-Miyaura Cross Coupling

References：

Chem. Sci. 2019, 10, 8202–8210.

J. Am. Chem. Soc. 2021, 143, 6165–6175

ACS Catal. 2021, 11, 14803–14810

Synlett 2022, 33, 898–902

RSC Adv. 2023, 13, 28652–28657.

Faraday Discuss. 2023, 241, 104–113.

Sonogashira Cross Coupling

Reference：Chem. Sci. 2022, 13, 430–438.

Yamamoto Coupling（Homocoupling）

Reference：

Chem. Lett. 2024, 53, upae056.

Buchwald-Hartwig Cross Coupling

References：

ACS Sustainable Chem. Eng. 2020, 8, 16577−16582

ChemSusChem 2022, 15, e202102132

Miyaura Borylation

Reference：

Beilstein J. Org. Chem. 2022, 18, 855–862.

引用元

Chem. Lett. 2023, 52, 333–336

Ni触媒NikkelC-Nクロスカップリング反応

Reference：

Angew. Chem. Int. Ed., 2023, 62, e202311531

Reactions with metal reagents

Magnesium（Grinard reagents）

Reference：

Nature Commun. 2021, 12, 6691.

LithiumLi

Reference：

Nature Synth. 2025, Just Accepted
DOI: 10.1038/s44160-025-00753-3

CalciumCa

Reference：

RSC Mechanochem. 2024, 1, 486–491.

Reference：

RSC Mechanochem. 2025, 2, 256–262.

Barium

Reference：

Chem. Sci. 2024, 15, 17453–17459.

Manganese

Reference：

Chem. Sci. 2023, 14, 499–505.

Reductions

Birch reduction

Li

Reference：

Angew. Chem. Int. Ed. 2023, 62, e202217723.

Na

Reference：

Chem. Sci. 2024, 15, 4452–4457.

Ca

Reference：

Chem. Lett. 2024, 53, upae060.

Nito group reduction

Reference：

Nature Synth. 2025, Just Accepted
DOI:

Phosphine oxide reduction

Reference：

RSC Mechanochem. 2024, 1, 250–254.

Radical reactions

Barium titanate

Reference：

Science. 2019, 366, 1500–1504.

Reference：

Angew. Chem. Int. Ed. 2020, 59, 22570–22576.

Reference：

J. Am. Chem. Soc. 2024, 146, 1062−1070

Fluorination reactions

Reference：

Green Chem. 2025, 27, 1771–1776.

Reference：

Synlett 2023, 34, 1419–1424

Compounds

Heterocyclic compounds（N・O・S）

Contains N

Contains O・S

Amines

Polycyclic aromatic hydrocarbons

Halogen compounds

FluorineF

ChlorineCl,Bromine Br,Iodine I

Organic phosphorus compounds

立体合わせる。

Organometallic reagents（Contains boron, silicon as metalloids）

Gringnard reagents（Mg）

Lithium reagents

Calcium reagents

Barium reagents

Manganese reagents

Organoboron compounds

Organosilicon compounds