TY - JOUR
T1 - Quantum reality in the selective reduction of a benzofuran system
AU - Coaviche-Yoval, Arturo
AU - Andrade-Jorge, Erik
AU - Pérez-González, Cuauhtémoc
AU - Luna, Héctor
AU - Tovar-Miranda, Ricardo
AU - Trujillo-Ferrara, José G.
N1 - Publisher Copyright:
© 2019 by the authors.
PY - 2019
Y1 - 2019
N2 - Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson's hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ωk) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (Pk+) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction.
AB - Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson's hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ωk) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (Pk+) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction.
KW - catalytic reduction
KW - electrophilic
KW - global reactivity
KW - local reactivity
KW - olefinic carbons
KW - selectivity
UR - http://www.scopus.com/inward/record.url?scp=85066871962&partnerID=8YFLogxK
U2 - 10.3390/molecules24112061
DO - 10.3390/molecules24112061
M3 - Artículo
C2 - 31151186
AN - SCOPUS:85066871962
SN - 1420-3049
VL - 24
JO - Molecules
JF - Molecules
IS - 11
M1 - 2061
ER -