Methods for the preparation of alkyl diaryl borinates and complexed diarylboronic acids

A method for preparing a compound of formula I:

• wherein A is O;
• W is Cp, where p is 0;
• Rb and Rc are connected by a phenyl ring optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, halogen, nitro, nitroso, aldehyde, carboxylic acid, amide, ester, or sulfate, and
• Rc and Re are connected by a phenyl ring optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, halogen, nitro, nitroso, aldehyde, carboxylic acid, amide, ester, or sulfate, where Ra is absent when A is O, and Rd is absent when p=0;
• Rf is hydrogen or is absent;
• and
• wherein Ar1 and Ar2 are independently thienyl or aryl, wherein aryl is optionally substituted at one or a plurality of positions with halogen, nitro, nitroso, lower alkyl, optionally substituted aryl, lower alkoxy, lower alkoxyalkyl, cycloalkyl, or cycloalkyl alkoxy, where each cycloalkyl group has from 3-7 members, and where any member of the aryl or cycloalkyl group is optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, halogen, nitro, nitroso, aldehyde, carboxylic acid, amide, ester, or sulfate, and
• wherein bond 1, bond 2, bond 3 and bond 4 are independently a single bond or a double bond, provided that when A is O, bond 1 is a single bond,
• said method comprising the step of:
• reacting an methyl diarylborinate of formula III with a compound of formula II to form the compound of formula I
• wherein the methyl diarylborinate of formula III and the compound of formula II are in a ratio of about 1 to about 0.9 equivalents respectively;
• and
• wherein the methyl diarylborinate of formula III is prepared by reacting about 1 equivalent of trimethylborate with about 2 equivalents of metalloorganic reagent.