(Chloromethyl)lithium: Efficient generation and capture by boronic esters and a simple preparation of diisopropyl (chloromethyl)boronate

Article abstract of DOI:10.1021/om00128a038

(Chloromethyl)lithium is efficiently generated and captured at -78°C by adding n -butyllithium to a mixture of iodochloromethane and a boronic ester in tetrahydrofuran, resulting in conversion of boronic esters, RB(OR′)₂, to their homologues, RCH₂B(OR′)₂, with retention of the configuration of the R group. With triisopropyl borate in place of the boronic ester, a high yield of diisopropyl (chloromethyl)boronate is obtained.