Borylations and Silylations of Alkenyl and Alkynyl Carbonyl Compounds Employing a Mild and Environmentally Friendly Cu(II) Catalyst

An environmentally friendly, operationally simple copper-amine catalyst system is disclosed. Using this catalyst system, electron deficient alkenes and alkynes with diverse functional groups are borylated and silylated in high yields and with short reaction times. In the case of electron deficient alkynes the identity of the electron withdrawing group controlled diastereoselectivity. Esters and amides exclusively form E-product, while aldehydes and ketones favor Z-product. Mechanistic insights into the catalytic cycle as well as origin of diastereoselectivity are discussed.

Name thesis:degree_name

Master of Science

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Tech

Year dc:date.issued

2014

Author dc:creator

• Calderone, Joseph Anthony III

Chair dc:contributor.committeechair

• Santos, Webster L.

Committee members dc:contributor.committeemember

• Tanko, James M.
• Gandour, Richard D.

• Copper Catalysis
• Silylation
• Borylation
• Green Chemistry
• Synthetic Methodology

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Dc Identifier Other

vt_gsexam:2706

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/47723