A New Family of Nucleophiles for Photoinduced, Copper-Catalyzed Cross-Couplings via Single-Electron Transfer: Reactions of Thiols with Aryl Halides Under Mild Conditions (O ° C)
Christopher Uyeda; Yichen Tan; Gregory C. Fu; Jonas C. Peters; Journal of the American Chemical Society 135 (2013) 9548–9552; doi:10.1021/ja404050f

data_4119993
_publ_section_title
;
 A New Family of Nucleophiles for Photoinduced, Copper-Catalyzed
 Cross-Couplings via Single-Electron Transfer: Reactions of Thiols with
 Aryl Halides Under Mild Conditions (O \% C)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9548
_journal_page_last               9552
_journal_paper_doi               10.1021/ja404050f
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C74 H62 Cu5 Na2 O16 S7'
_chemical_formula_weight         1795.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.530(3)
_cell_angle_beta                 71.368(2)
_cell_angle_gamma                61.411(2)
_cell_formula_units_Z            2
_cell_length_a                   15.7407(6)
_cell_length_b                   15.7841(6)
_cell_length_c                   19.5588(8)
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.46
_cell_measurement_theta_min      2.18
_cell_volume                     4026.9(3)
_computing_cell_refinement       'SAINT-Plus v7.66A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2010.7-0 (Bruker-AXS, 2010)'
_computing_data_reduction        'SAINT-Plus v7.66A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_sigmaI/netI    0.0964
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            150135
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         35.63
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    1.553
_exptl_absorpt_correction_T_max  0.8602
_exptl_absorpt_correction_T_min  0.7363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker-AXS, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1826
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         9.481
_refine_diff_density_min         -2.258
_refine_diff_density_rms         0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     874
_refine_ls_number_reflns         33743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.2124
_refine_ls_R_factor_gt           0.1403
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1909P)^2^+59.8789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3776
_refine_ls_wR_factor_ref         0.4232
_reflns_number_gt                18860
_reflns_number_total             33743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404050f_si_002.cif
_cod_data_source_block           chu70
_cod_database_code               4119993