Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and Heteroaryl Chlorides, Using Pd Complexes of t-Bu2(p-NMe2C6H4)P: Understanding the Structure-Activity Relationships and Copper Effects
Xiaotao Pu; Hongbo Li; Thomas J. Colacot; Journal of Organic Chemistry 78 (2013) 568–581; doi:10.1021/jo302195y

data_4027849
_publ_section_title
;
 Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and
 Heteroaryl Chlorides, Using Pd Complexes of t-Bu2(p-NMe2C6H4)P:
 Understanding the Structure-Activity Relationships and Copper Effects
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              568
_journal_page_last               581
_journal_paper_doi               10.1021/jo302195y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C32 H56 N2 P2 Pd'
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
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_atom_sites_solution_primary     direct
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_cell_angle_alpha                101.924(10)
_cell_angle_beta                 99.082(9)
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_cell_formula_units_Z            2
_cell_length_a                   8.375(4)
_cell_length_b                   12.038(6)
_cell_length_c                   18.163(9)
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_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.57
_cell_measurement_theta_min      2.35
_cell_volume                     1676.7(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       \w
_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  0.0765
_diffrn_reflns_av_sigmaI/netI    0.1124
_diffrn_reflns_limit_h_max       9
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_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.9114
_exptl_absorpt_correction_T_min  0.7967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_refine_diff_density_max         2.044
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.2024
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302195y_si_001.cif
_cod_data_source_block           jmca014
_cod_original_cell_volume        1676.6(14)
_cod_database_code               4027849