Chemoselective synthesis and evaluation of β-oxovinylarsines as an arsenic synthetic precursor

• Main Authors: Tay, Wee Shan, Li, Yongxin, Lu, Yunpeng, Pullarkat, Sumod A., Leung, Pak-Hing
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2022
• Subjects: Science::Chemistry; Catalysts; Isomers
• Online Access: https://hdl.handle.net/10356/155189
• Institution: Nanyang Technological University

β-Oxovinylarsines are introduced as a stable and highly functionalized bench-top arsenic precursor. Stereoselective syntheses furnished geometrically pure cis- A nd trans-isomers from the same ynone under different conditions. The organic Michael acceptor backbone allowed β-oxovinylarsines to be easily applied to conjugate-addition reactions, and β-oxovinylarsines were reactive to nucleophiles, electrophiles, and transition metals. Unlike other arsenic precursors which are toxic or volatile or have low reactivity, β-oxovinylarsines bear a well-defined organic backbone that confers both stability and known reactivity. Remarkably, β-oxovinylarsines were also compatible with organometallic catalysts and did not decompose or deactivate the catalyst by chelation.