TY - JOUR

T1 - Vinylation of alcohols, thiols and nitrogen compounds using a stoichiometric amount of in situ generated acetylene

AU - Ледовская, Мария Сергеевна

AU - Воронин, Владимир Владимирович

AU - Резниченко, Анна Александровна

AU - Резниченко, Екатерина Александровна

PY - 2025/2/8

Y1 - 2025/2/8

N2 - In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of a broad scope of substances, including alcohols, thiols, and nitrogen compounds. The key advantage of the proposed method is the use of calcium carbide as a robust acetylene source in a stoichiometric ratio to the substrates. Lacking the requirement of acetylene excess, the developed protocol is safe, highly economic, and limits waste production. The procedure allows for a large variety of O-,S-,N-vinyl compounds to be synthesized in up to quantitative yields. Our methodology is scalable, allowing us to obtain vinyl derivatives in Gram-scale quantities. We also demonstrated the significant synthetic value of our approach by performing a label-economic synthesis of 13C2-labeled vinyl derivatives using calcium carbide-13C2. In our well-optimized process, the conversion of Ca13C2 reached 89%.

AB - In this work, we developed a highly efficient and versatile environmentally benign methodology for the vinylation of a broad scope of substances, including alcohols, thiols, and nitrogen compounds. The key advantage of the proposed method is the use of calcium carbide as a robust acetylene source in a stoichiometric ratio to the substrates. Lacking the requirement of acetylene excess, the developed protocol is safe, highly economic, and limits waste production. The procedure allows for a large variety of O-,S-,N-vinyl compounds to be synthesized in up to quantitative yields. Our methodology is scalable, allowing us to obtain vinyl derivatives in Gram-scale quantities. We also demonstrated the significant synthetic value of our approach by performing a label-economic synthesis of 13C2-labeled vinyl derivatives using calcium carbide-13C2. In our well-optimized process, the conversion of Ca13C2 reached 89%.

KW - acetylene

KW - vinylation

KW - vinyl group

KW - alcohols

KW - thiols

KW - amines

KW - calcium carbide

KW - acetylene

KW - calcium carbide

KW - vinylation

KW - amines

KW - thiols

KW - alcohols

KW - vinyl group

UR - https://www.mendeley.com/catalogue/004a6697-cb6c-3558-851c-168fe038d379/

U2 - 10.3390/org6010005

DO - 10.3390/org6010005

M3 - Article

VL - 6

JO - Organics

JF - Organics

SN - 2673-401X

IS - 1

M1 - 5

ER -