TY - JOUR

T1 - Organoboron Derivatives of 1,8-Bis(dimethylamino)naphthalene

T2 - Synthesis, Structure, Stability, and Reactivity

AU - Bardakov, Victor G.

AU - Yakubenko, Artyom A.

AU - Verkhov, Valeriy A.

AU - Antonov, Alexander S.

N1 - Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/6/27

Y1 - 2022/6/27

N2 - A series of ortho-, meta-, and para-boronic acids and their pinacol esters of 1,8-bis(dimethylamino)naphthalene (DMAN), including the very first naphtho[1,8-cd][1,2,6]oxadiborinine-based proton sponge, were synthesized with moderate to good yields. The ease of deborylation of sterically hindered ortho-boronic acids of DMAN was demonstrated. DMAN-based 3,6-diboronic acid and its pinacol ester─valuable precursors for meta-derivatives of the naphthalene proton sponge─were prepared and utilized for the synthesis of 3,6-diiodo-DMAN. Obtained acids and esters were tested for common palladium and copper catalyzed couplings.

AB - A series of ortho-, meta-, and para-boronic acids and their pinacol esters of 1,8-bis(dimethylamino)naphthalene (DMAN), including the very first naphtho[1,8-cd][1,2,6]oxadiborinine-based proton sponge, were synthesized with moderate to good yields. The ease of deborylation of sterically hindered ortho-boronic acids of DMAN was demonstrated. DMAN-based 3,6-diboronic acid and its pinacol ester─valuable precursors for meta-derivatives of the naphthalene proton sponge─were prepared and utilized for the synthesis of 3,6-diiodo-DMAN. Obtained acids and esters were tested for common palladium and copper catalyzed couplings.

UR - http://www.scopus.com/inward/record.url?scp=85132544022&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/a51755ab-12b3-3631-8da0-30e6a486bab4/

U2 - 10.1021/acs.organomet.2c00115

DO - 10.1021/acs.organomet.2c00115

M3 - Article

AN - SCOPUS:85132544022

VL - 41

SP - 1501

EP - 1508

JO - Organometallics

JF - Organometallics

SN - 0276-7333

IS - 12

ER -