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. 2023 Dec 29;26(1):360–364. doi: 10.1021/acs.orglett.3c04030

Scheme 1. Synthesis of Aryl Bridge-Substituted BCBs.

Scheme 1

Reaction conditions, unless stated otherwise: 2a or 2b (0.20 mmol, 1.0 equiv); 1. Lithiation: at-BuLi (0.22 mmol, 1.1 equiv, 1.1–1.3 M in pentane, THF, −78 °C, 1.5 h; bs-BuLi (0.22 mmol, 1.1 equiv, 1.1–1.5 M in cyclohexane), THF, −45 °C, 3.0 h; 2. Transmetalation/coupling: ZnCl2 (0.22 mmol, 1.1 equiv), THF, −78 °C (or −45 °C) to rt; Pd(dba)2 (15 mol %), CyJPhos (30 mol %), R–I (0.4 mmol, 2.0 equiv) THF, 1 h, 20 °C; 1 d, 65 °C. cStructure of 3l from single-crystal X-ray diffraction studies (displacement ellipsoids drawn at 50% probability). dThe reaction was conducted on a 1 mmol scale.