Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates.
Using a recently discovered precatalyst, the first Pd-catalyzed Suzuki-Miyaura reactions using aryl sulfamates that occur at room temperature are reported. In complementary work, it is demonstrated that a related precatalyst can facilitate the coupling of aryl silanolates, which are less toxic and reactive nucleophiles than boronic acids with aryl chlorides. By combining our results using modern electrophiles and nucleophiles, the first Hiyama-Denmark reactions using aryl sulfamates are reported.
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520, United States.
Patrick R
PR
Melvin
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520, United States.
Nilay
N
Hazari
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520, United States.
Megan Mohadjer
MM
Beromi
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520, United States.
Hemali P
HP
Shah
Department of Process Chemistry, Merck Research Laboratories , Rahway, New Jersey 07065, United States.
Michael J
MJ
Williams
D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*
D006841:Hydrocarbons, Aromatic; D012821:Silanes; D013451:Sulfonic Acids; D010165:Palladium; C005741:sulfamic acid