Catalyst-free hydrophosphination of alkenes in ethanol
Abstract
Hydrophosphination generates regioselective P-C bonds efficiently as medical, agricultural, and electronic industries demand. In the literature, practical constraints are met with high loading of toxic, air-sensitive, and highly tailored metal catalysts. This work demonstrates catalyst-free hydrophosphination producing alkyl tertiary phosphines without metal in ethanol, a green solvent. This one pot reaction of a Michael acceptor and simple, secondary phosphine has proceeded to completion at room temperature at rates comparable to those run with metal catalysts. Ongoing work aims to justify observed photo dependence in reactions of bulkier substrates, and determine a mechanism to leverage more diverse alkenes for this transformation.
Primary Faculty Mentor Name
Rory Waterman
Status
Undergraduate
Student College
College of Arts and Sciences
Program/Major
Chemistry
Primary Research Category
Physical Science
Catalyst-free hydrophosphination of alkenes in ethanol
Hydrophosphination generates regioselective P-C bonds efficiently as medical, agricultural, and electronic industries demand. In the literature, practical constraints are met with high loading of toxic, air-sensitive, and highly tailored metal catalysts. This work demonstrates catalyst-free hydrophosphination producing alkyl tertiary phosphines without metal in ethanol, a green solvent. This one pot reaction of a Michael acceptor and simple, secondary phosphine has proceeded to completion at room temperature at rates comparable to those run with metal catalysts. Ongoing work aims to justify observed photo dependence in reactions of bulkier substrates, and determine a mechanism to leverage more diverse alkenes for this transformation.
