TY - JOUR AU - Masuya, Yoshihiro; Kawashima, Yuki; Kodama, Takuya; Chatani, Naoto; Tobisu, Mamoru TI - Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2′-Bis(methylthio)-1,1′-Biaryl Derivatives through Cleavage of Two Carbon–Sulfur Bonds SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 17 SP - 1995 EP - 1999 ET - 2019/01/14 DA - 2019/10/07 KW - C–S cleavage KW - C–O cleavage KW - metathesis KW - thiophene AB - A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1611974 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611974 ER -