Identification of a boron-containing intermediate in the boron tribromide mediated aryl propargyl ether cleavage reaction.
An alternate reaction mechanism for the boron tribromide mediated deprotection of aryl propargyl ethers based on the isolation of a key boron-containing byproduct is proposed. On the basis of the new mechanistic insight, we discovered that HBBr(2) x SMe(2) can also be used for cleaving aryl propargyl ethers.
Yao
Min-Liang
ML
Department of Chemistry, The University of Tennessee, Knoxville, 37996-1600, USA.
Reddy
Marepally Srinivasa
MS
Zeng
Wenbin
W
Hall
Kelly
K
Walfish
Ingrid
I
Kabalka
George W
GW
D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D014753:Vinyl Compounds / Q000138:chemical synthesis
D000475:Alkenes; D000480:Alkynes; D001896:Boron Compounds; D001965:Bromides; D004987:Ethers; D006842:Hydrocarbons, Brominated; D014753:Vinyl Compounds; C531209:propargyl ether