Journal
ACS CATALYSIS
Volume 10, Issue 1, Pages 352-357Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b03667
Keywords
B(dan); borate; boronic acid; cross-coupling; palladium; Suzuki-Miyaura
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Funding
- Foundation for Interaction in Science and Technology (FIST), Japan
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We report a Suzuki-Miyaura cross-coupling reaction of 1,8-diaminonaphthalene (dan)-protected arylboronic acids in the presence of KOt-Bu, which does not require the removal of the dan moiety. Notably, the use of aryl-B(dan) in the Suzuki-Miyaura reaction provides a complementary solution to the protodeboronation problems. The base KOt-Bu plays a crucial role for the promotion of these cross-coupling reactions as it enables the formation of a borate salt. This reaction protocol was extended to the one-pot sequential Suzuki-Miyaura cross-coupling reaction of 4-[(pin)B]C6H4-B(dan), wherein the less reactive aryl-B(dan) moiety was cross-coupled preferentially.
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