Slow release of organoboronic acids in cross-coupling reactions

Eric P Gillis; Martin D Burke; David M Knapp

Slow release of organoboronic acids in cross-coupling reactions

Eric P Gillis (Inventor), Martin D Burke (Inventor), David M Knapp (Inventor)

Research output: Patent

Abstract

A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R1—B-T (I);where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

Original language	English (US)
U.S. patent number	9845317
Filing date	4/29/16
State	Published - Dec 19 2017

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title = "Slow release of organoboronic acids in cross-coupling reactions",

abstract = "A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R1—B-T (I);where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.",

author = "Gillis, {Eric P} and Burke, {Martin D} and Knapp, {David M}",

note = "FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT The subject matter of this application may have been funded in part under a research grant from the National Science Foundation under Grant Number Career 0747778, and under a research grant from the National Institutes of Health under Chemical Biology Interface Training Number 1-492576-510000-191788. The U.S. Government may have rights in this invention.; 9845317",

year = "2017",

month = dec,

day = "19",

language = "English (US)",

type = "Patent",

}

TY - PAT

T1 - Slow release of organoboronic acids in cross-coupling reactions

AU - Gillis, Eric P

AU - Burke, Martin D

AU - Knapp, David M

N1 - FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT The subject matter of this application may have been funded in part under a research grant from the National Science Foundation under Grant Number Career 0747778, and under a research grant from the National Institutes of Health under Chemical Biology Interface Training Number 1-492576-510000-191788. The U.S. Government may have rights in this invention.

PY - 2017/12/19

Y1 - 2017/12/19

N2 - A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R1—B-T (I);where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

AB - A method of performing a chemical reaction includes reacting a compound selected from the group consisting of an organohalide and an organo-pseudohalide, and a protected organoboronic acid represented by formula (I) in a reaction mixture:R1—B-T (I);where R1 represents an organic group, T represents a conformationally rigid protecting group, and B represents boron having sp3 hybridization. When unprotected, the corresponding organoboronic acid is unstable by the boronic acid neat stability test. The reaction mixture further includes a base having a pKB of at least 1 and a palladium catalyst. The method further includes forming a cross-coupled product in the reaction mixture.

M3 - Patent

M1 - 9845317

Y2 - 2016/04/29

ER -

Slow release of organoboronic acids in cross-coupling reactions

Abstract

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